Labor Day weekend on Cape Cod feels like summer’s final standing ovation. The beaches are still busy, the shops are alive, and the weather is right in that sweet spot between hot and crisp. It’s one of the last big weekends before fall routines kick in, and Cape Cod brings it all. If you’re thinking about a Labor Day escape, now’s the time to start planning it right.

Catch the Good Weather

Early September is Cape Cod at its most comfortable. The heat has mellowed, but the ocean still holds warmth. Morning walks feel fresh instead of sweaty, and sunset dinners are actually enjoyable without being swarmed by peak summer crowds. It’s the kind of weather that makes you want to stay outside all day, whether you’re on the sand, on the water, or on a patio. It’s why we call is “Locals Summer”!

Labor Day weekend brings people in, but it doesn’t feel too chaotic. It’s busy in a good way. Restaurants are full, beach parking fills up, and there’s a definite buzz, but you can still find your space. You can actually hear the ocean. You can move through town without a wall of bodies. You’re still in the middle of it all, just with a little more breathing room.

Keep Exploring

Cape Cod doesn’t run out of things to do. If anything, Labor Day brings an extra layer of energy to it. Towns like Provincetown, Chatham, and Orleans host live music, food pop-ups, and weekend events that make every corner feel like it’s celebrating. The beach is still the main draw, but there’s plenty happening beyond the shore.

Check out harbor tours and boat rentals if you want time on the water without the full commitment of a whale watch. Try the Cape Cod Rail Trail for a bike ride through some of the most scenic parts of the peninsula. Spend an afternoon bouncing between local breweries or tracking down the best lobster roll you’ve ever had. No matter your pace, there’s something here to match it.

Plan With the Tides

The Cape runs on tides, so if you’re planning beach days or water activities, timing matters. At low tide, sandbars stretch out and create new places to explore on foot. High tide is ideal for floating, kayaking, or paddleboarding. Knowing the tide schedule can be the difference between a quick dip and a full beach day, so keep an eye on it as you map out your weekend.

It’s also a great time to make the most of early mornings and golden hour. Late summer sunrises over the water are unbeatable, and evening walks by the bay give you a front row seat to some of the best sunsets on the East Coast.

Rain or Shine

If you catch a cloudy day or quick shower, don’t stress. Cape Cod is still full of places to explore indoors. You’ve got art galleries in Provincetown, antique shops across Barnstable, and museums like the Cape Cod Museum of Natural History or the John F. Kennedy Museum in Hyannis. You can also catch a film at the Wellfleet Drive-In or book a spa appointment and turn the day into a recharge moment. The point is, even if the forecast changes, your plans don’t have to fall apart. The Cape has a way of making every kind of day feel worth it.

Where You Stay Changes Everything

One of the best ways to make your Labor Day trip feel like a true vacation is to stay somewhere that lets you unwind without compromise. Pretty Picky Properties offers a wide selection of Cape Cod vacation rentals across towns like Brewster, Yarmouth, Dennis, and Orleans. Whether you’re looking for a luxury beachfront home, a pet-friendly cottage, or a spacious house for a big family group, we have a property that fits.

Every home comes fully equipped so you can settle in quickly and start enjoying your time. From outdoor showers and chef’s kitchens to patios, pools, and waterfront views, these rentals are the reason you’ll want to come back. When you book with Pretty Picky Properties, you’re giving yourself a space that fits your trip, your crew, and your style.

Start Planning Your Labor Day Weekend on Cape Cod Today

Labor Day weekend is your chance to send off summer with something better than a backyard BBQ. Cape Cod is calling, and this is the time to answer it. Book your Labor Day rental now with Pretty Picky Properties and make this last weekend of summer one of the best ones yet.

When you first began planning your Cape Cod vacation, the odds are that you imagined yourself spending minutes, hours, even entire days at the beaches that have made us famous, and while we know that will not change, we hope that after reading about hiking on Cape Cod you will also begin to imagine a beautiful hike on a glorious day.

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Just being outside on our island home is an adventure in wow, but as you stroll along trails where the wildflowers bloom, hike to ponds and waterways that offer a quieter serenity than the roar of the ocean, and saunter through preserves and conservation areas where you will share the experience with a variety of wildlife, the flirtation you began with Cape Cod many years ago will bloom into a full fledged love affair.

And, as if there isn’t enough to fall in love with on this beautiful and historic patch of real estate and nature, coming home to Pretty Picky Properties will add an extra layer of O.M.G. to your vacation experience and this guide will help you make sure you don’t miss a single moment of adventure and fun.

What to Pack for Your Hiking Adventure

If you are planning nothing more than a walk around the neighborhood your Pretty Picky Properties Cape Cod escape is located in, you won’t really need to pack anything special, just wear what you would while walking around your own block back home.

A hike through the wilderness, however, is another matter entirely, and yes, you should dress appropriately. Comfortable walking shoes or hiking boots are the first order of business, and if you go for the boots, know that you are doing so for the purpose of supporting your ankles, because even though there are 10 different varieties of snakes that you may come across during your hike, none are venomous.

Moisture wicking shirts and socks are important as are light pants, and because you want to reflect the sun away from your body, make sure that your clothing is light colored. Wide-brimmed hats and sunglasses will help guard against the brightness of the sun, and just as you would at the beach, be sure to generously slather your exposed skin with sunscreen.

The Rules of the Cape Cod Hiking Trails

Now we know you are taking a walk on the wild side, but civilized hikers will always follow the rules of the trail on Cape Cod, ensuring safety for the hiker and continued beauty for the countryside your hiking journey will be exploring.

Rule Number 1: Always let someone know your hiking plans.

Cape Cod isn’t that large, but you could still get lost, or if you twist an ankle or something, having someone know your plans can ensure that the alarm will be sent up when you don’t return on schedule.

Rule Number 2: Carry Plenty of Water

Thankfully, this isn’t the desert, or you wouldn’t even be considering a summer hike, but staying hydrated is important no matter what part of the world you are exploring. We have found that hydration packs, often known as Camelbaks, are the easiest way to carry enough water for your hike.

Rule Number 3: Stay on Marked Paths

Staying on marked trails isn’t just important for your safety, it is vital for the protection of the land, especially when wandering along dunes or swamp areas.

Rule Number 4: Do Not Interact with the Wildlife

Most of the wildlife you will come across will be harmless, and some will be cute and fuzzy, but they need to stay wild for their safety, and that will not happen if you feed them. We encourage you to take as many pictures as you want, but from a distance, and without any food being exchanged for poses.

And Now it is Time for the No’s

We try to stay positive on Cape Cod, but there are some things that are forbidden and that list includes no public nudity, no open fires, and no glass containers while exploring the Cape Cod National Seashore.

Now For the Fun Stuff

Now that you are dressed correctly, understand how to stay safe, and know the rules of the trails, let’s get to it. The first trails we want to talk about are the shorter, easier ones, designed more for a stroll through the beauty of the Cape Cod countryside than for exercise or adventure.

Fort Hill in Eastham

Short and sweet, the 1-mile Fort Hill Loop in Eastham offers a parking area across from the Captain Penniman House, located at 70 Fort Hill Road. Reminiscent of a hike through the English countryside, this trail will take you through open fields, connecting with another trail we want to talk about, the Red Maple Swamp Trail. Offering stunning views of some of our favorite natural wonders including the Nauset Marsh Area, this trail is good for hikers of all skill levels and shouldn’t take more than half an hour to finish if you hike straight through, but we suggest scheduling in time to do a little birdwatching or taking advantage of the many photo opportunities that will come along the way.

The Red Maple Swamp Trail

Accessed by the Fort Hill Trail, the Red Maple Swamp Trail shines brightest during the fall when the leaves change, but it is a fun walk no matter what time of year you take it. Not even a mile in length, the trail offers a boardwalk that ambles through the Red Maple Swamp and offers seasonal restrooms near Hemenway Landing, a popular spot for kayakers that you may want to come back and explore with a kayak you’ve rented from Paddle Cape Cod MA, 4730 State Highway Building B, also in Eastham.

The Perfect Places to Relax in Eastham

Even though neither of these Eastham trails is particularly difficult, you may still be relieved to realize that our Pretty Picky Properties sanctuaries are especially close. Offering water views and luxury amenities, these spaces are the perfect ones for getting off your feet and getting to the very important business of relaxing! Providing wine refrigerators, blenders, and coffee makers (or Keurigs), your hydration needs will all be met as well!

Browse our Eastham Vacation Rentals Here!

Let’s Explore the Conservation Areas

The natural landscape of Cape Cod is worthy of preserving, and there are many conservation areas found throughout, each offering its own trail that will help you examine what’s being protected in an up-close and personal way.

The Long Pond Conservation Area Trail

The Long Pond Conservation Area is a protected area that revolves around another local treasure, Long Pond in Barnstable, more specifically in the Marston Mills village. The 1.4-mile loop trail that wanders through the conservation area is a relatively easy one, taking hikers through meadows filled with wildflowers, cool green forests, and along the banks of Long Pond. Serene, quiet, and not as well-traveled as some of our other trails, this loop may be the one that pushes you over that edge of emotion, the one that will make you fall deeply and irrevocably in love with Cape Cod. Leashed dogs are allowed on this trail, and interpretive signs are placed all along the path, helping hikers understand the flora and fauna they are seeing.

At Home in Marston Mills

As you might expect, the village of Marston Mills is also the location of some of our Pretty Picky Properties. We mentioned that the Long Pond Conservation Area Trail is dog-friendly, not just because you may run across other hikers with puppies you can pet, but because we also offer some pet-friendly homes in Marston Mills, and we encourage you to bring the entire family along on this Massachusetts trip of a lifetime. And if you are feeling especially warm at hike’s end, we also offer some properties with pools in this Barnstable Village, so why not take a swim and quickly cool down?

Browse our Marston Mills Vacation Rentals Here!

Spruce Hill Conservation Area Loop

We’re heading to Brewster for our next conservation area trail, taking some time to explore all that the Spruce Hill Conservation Area Loop has to offer. Named for the grove of mature Norway Spruce trees that provide cool shade and a hushed ambience, the loop comes in at just under a mile at .8 and its parking area can be found off Route 6A, just .3 miles away from the end of what used to be the Cape Cod Sea Camp’s entrance. Featuring mature oaks in addition to its namesake pines, the trail leads hikers to a quiet beach, one that doesn’t offer a lifeguard, but will make a wonderful photo opportunity.

Brewster Beauties

We offer a large number of properties in Brewster, ranging in size from cozy 2-bedroom cottages to grand 10-bedroom estates, with most offering beach or pond views. Don’t ask us which view is more preferable, we just love a water view no matter how big or how small, but we will admit that properties that sit on ponds tend to feel a little more secluded, a little more private, and even the largest homes will feel a little more cozy! Often tucked into a wooded area and featuring gardens filled with colorful flowers, there is a different mood that can be felt in a home by a pond, but it will still be serene and quiet.

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Worth the Extra Effort

The trails we have listed so far will take you through some of the most stunning land and seascapes on Cape Cod, but none of them have offered much of a challenge, so next up on our tour of Cape Cod trails are some more difficult hikes. These hikes will be worth the extra effort and will bring you many, many, many exciting examples of what makes Cape Cod one of America’s favorite travel destinations.

Great Island Trail

Great Island is neither an island nor a village, but is what the peninsula area of Wellfleet is known as, which is also the location of one of Cape Cod’s longest trails. The Great Island Trail ranges between 3.9 miles (if you take the loop) and 8.8 miles in length. The trail begins at the corner of Griffin Island and Chequessett Neck Road with a parking area located on Chequessett Road, and a picnic area can be found nearby, so be sure to pack a cooler in your rental car to enjoy at the end of your hike. This trail takes hikers along sandy beaches, up log steps, and some areas may be underwater at high tide, making it a tad more difficult than packed dirt, pavement, or the boardwalks of other trails, and because the elevation is higher than on other spots on Cape Cod, the views you experience will be stunning. Some parts of the trail lead to what was once a colonial-era tavern site, which although it is no longer there, still offers echoes and whispers of the past.

The Wonders of our Wellfleet Escapes

After the long hike along the Great Island Trail, you will be more than ready to get off your feet and into the bubbling waters of a hot tub, and yes, you guessed it, some of our Wellfleet escapes offer that luxury amenity. Wellfleet is a mariner’s town, known for its pristine beaches, oyster production, and its annual Oyster Fest, so of course, most of our properties in Wellfleet will be located on or near the water. Relaxing, luxurious, and designed to make guests feel happily at home even as they are miles away from their own, these Wellfleet sanctuaries will offer joy around every corner.

Browse our Wellfleet Vacation Rentals Here!

A Love Affair That Never Ends

When you fall in love with Cape Cod, be prepared for a love affair that never ends, enticing you to visit time and time again, staying in our Pretty Picky Properties Massachusetts retreats. Reserve your favorite escape today and discover how all trails lead home to luxury, style, and all the comforts of home!

There will be a lot of things to do during your vacation on Cape Cod, and because we at Pretty Picky Properties believe you can never have enough fun, we thought today would be a good time to talk about the different summer events that take place here every year. From arts festivals to holiday celebrations, these events add an extra shine to your getaway, and as an added bonus, coming home to our summer sanctuaries at the end of each event will give you even more to smile about. This guide to some of the best summer Cape Cod events, and our home sweet vacation homes located nearby, will help you fill in all the blank spaces on your Cape Cod Itinerary!

Brewster Summer Arts & Crafts Festival, 2 Days in Late July, Drummer Boy Park

The craftsmen and women of Brewster get together every summer to give visitors and locals something fun and beautiful to shop for, and if your visit brings you here at the end of July, this event should not be missed. Our guests especially love the treasures they find while meandering through the aisles of this seaside expo, offering arts of all genres, crafts of all styles, and specialty foods that will make you wish you had enough room in your luggage to purchase all each vendor has to sell, including balsamic vinegars that can make a captivating marinade for the fish you may have caught during your leisure moments in Brewster. The event is free to attend, and if you are staying in one of our pet-friendly rentals, leashed dogs are invited to attend as well!

Our Brewster Retreats

Brewster was once home to over a dozen sea captains, giving it its nickname as “the sea captain’s town,” and although we don’t think any sea captains lived in our Brewster properties, we’re sure they would have wished that they could have! Offering homes with water views and charming cottages that are tucked away in family neighborhoods (none of which are far from the beach!), your stay in these retreats will be exactly what you dreamed a Cape Cod escape could provide. Our larger homes may provide private pools, large kitchens with center islands, and state-of-the-art televisions that you never turn on. And our smaller cottages may provide sandy beaches for their backyards, outdoor showers, and rocking chairs placed on porches where the views of the sunset are simply delightful!

Browse our Brewster Vacation Rentals Here!

Independence Day Celebration in Chatham

We love a parade, and Chatham’s 4th of July Parade is one of the oldest in the country, with the first procession taking to the streets of our all-American town in 1908, and after more than a hundred years, we have learned more than a few things about what makes a parade special! Offering a different theme every year, this parade features marching bands, local heroes, and a collection of classic cars, as well as an old fire engine that never fails to charm. There will be floats decorated to match the theme, dogs in the back of pickup trucks, and kids on bikes; everything you love about a small town parade. After the parade, which begins at 9:30 AM, guests can explore all manner of family-friendly events, including games, carnival rides, delicious foods, and, of course, end the day with a fireworks spectacular that will make your children’s eyes sparkle, and your heart feel full!

Our Chatham Sanctuaries

The Chatham Lighthouse is perhaps the top attraction in our town, but our Pretty Picky Properties Chatham sanctuaries run a very close second, offering all the comforts of home and luxuries that we think all our guests deserve to explore. Just as in Brewster, you may find swimming pools in the backyards, and many of these spaces will offer sea views, but there is more to discover when you choose to stay in these homes. Gather round the fire pit in the backyard on a cool night, reveling in family, and being amazed at how vast that Massachusetts sky can be.

Front porch life is as important in small towns as backyard play, and as you sit in one of the Adirondack chairs lined up on the front porch, sipping iced tea and watching children play and neighbors help each other out, the friendliness you experience here will make you wish you could call Chatham home! Inside, guests may discover slipcovered sofas, brick fireplaces, and separate dining rooms that invite occupants to play board games on quiet nights when you just don’t want to go out on the town!

Browse our Chatham Vacation Rentals Here!

Cape Cod Hydrangea Festival in Hyannis, July, Main Street Hyannis

Even those who have never been to Cape Cod before associate the beautiful hydrangea with it, charmed by its nearly plate-sized blooms that come in 5 beautiful colors: white, pink, purple, blue, and the little-known red hydrangeas.

Those beautiful flowers hold a place in our hearts and can often be seen clustered by front doors or creating an enchanted garden in most backyards of Cape Cod, and in July, the Cape Cod Hydrangea Festival celebrates this beautiful flower. Held in Hyannis, summer home to the Kennedys, the festival lasts for 10 days, with the highlight of the event being the daily tours of local gardens that are offered.

This especially gives tourists a peek into life on Cape Cod, often making them yearn for their own hydrangea garden, and if this is something that sounds wonderful to you, workshops given by knowledgeable gardeners and horticulturalists will help you learn the secrets of the blooms and perhaps start your own garden at home.

Pretty Picky Properties in Hyannis

The Kennedy compound is what most people think about when Hyannis comes up in conversation, and although that is our claim to fame, Hyannis is more than a playground for a former president’s family. It’s home for regular families, and when you choose Pretty Picky Properties in Hyannis, it will be your home sweet vacation home.

Offering some pet-friendly spaces that will allow the entire family to join in the fun, the properties we offer here will feel like home and as you enjoy a picnic for two or play board games with the family while gathered round large dining room tables, the large backyards may be calling your name.

Some overlook the Hyannisport Golf Club, a private course offering a long history, including the fact that yes, JFK did play there during his summers on Cape Cod. And even though the course is private, you will still enjoy the views from large patios and quite possibly be able to practice your short game as some Hyannis homes feature putting greens in the backyards.

Browse our Hyannis Port Vacation Rentals Here!

Yarmouth Sand Sculpture Trail, June, Multiple Locations Throughout Yarmouth

Chances are, your kiddos are going to beg to build sandcastles on the beach with you, but when you see the competition, you may be a little afraid to say yes. The Yarmouth Sand Sculpture Trail takes place daily in June, offering stunning representations of the ordinary and the extraordinary, all created from the mixture of sand and water.

There are 30 sculptures placed in various locations throughout town, all created by nationally renowned artist Sean Fitzpatrick and his beautiful wife. Whimsical creations may include a lobster sitting in an armchair sipping a martini, a giant fish holding a boy upside down as if the fish is posing with his catch, octopus, mermaids, even a classic Ford truck.

The Fitzpatricks tend to make their way to Cape Cod about mid-May, working 10-hour days to try and complete their masterpieces by the end of the third week in June. If you arrive early enough, you may even be able to catch the artists at work, a fascinating experience that can almost help you learn how to make your own sandcastles with your kids!

Lazy Days in Our Yarmouth Escapes

Life in Yarmouth moves at a slower pace, at least, the hours spent at home in our area retreats, and with many of our spaces offering water views, you can be sure that you will spend much of your trip sipping chardonnay, rocking on rocking chairs, and letting the call of the sea be answered by your soul.

These homes carry the serenity of those seas in their very center, providing spots to sit and contemplate all that is wonderful about your life. Bare feet covered in fine granules of sand, messy hair carelessly made into a bun on the top of your head, swimsuits, and sunburned noses are the uniform of your stay, and we know that this look suits everyone.

Maybe it is the nighttime moments that are most special, spent sleeping on premium beds as the television plays low. Maybe the windows of your Yarmouth escape will be open, allowing the sound of the surf and the scent of salt air to play a tranquil lullaby to lead you into the best sleep of your life. Every moment at home in Yarmouth will be your favorite moment when you choose Pretty Picky Properties!

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Wellfleet Shellfish Farm Tours, End of June Through Mid-October, Wellfleet Harbor

Offering an up-close and personal look at some of the 108 aquaculture farms in the area, the Wellfleet Shellfish Farm Tours really are a unique adventure that shines brighter simply because you are enjoying it on Cape Cod. Walk out into the waters where a variety of shellfish are farmed and harvested, learn all about their life cycles, and discover why they taste so darn good. Shucking and slurping are an integral part of the shellfish farm tours, and once you start, you may never want to stop again. Or, at the very least, you may rue having to leave because you know that although you may have chosen one of our Wellfleet escapes for your summer accommodations, you soon will have to return to your real home, far, far, far away from the best shellfish in the world!

Yes, We are in Wellfleet as Well!

Even as we keep up with modern amenities such as coffee shops with internet and gift shops that sell a little bit of everything, it is our link to the past that makes Wellfleet so special, and one of your favorite adventures may be a blast from the past, a night at the Wellfleet Drive-In Theater! In the daytime, it serves as a flea market on weekends in the summer, and of course, a place to watch movies and fog up your windows at night. But it is the fun moments you will have at home in our Wellfleet retreats that will make this trip a memorable one, offering comfortable living spaces, modern amenities, and in some cases, bubbling hot tubs perched on large back patios, offering another way to relax and play. Our homes in this area are inviting, welcoming, and warm, filled with light and all the charm Cape Cod is known for offering, giving you a vacation experience you won’t be able to, or even want to, ever forget!

Browse our Wellfleet Vacation Rentals Here!

Father’s Day Car Shows, Spring Sheep Festivals, and so Much More!

Summer on Cape Cod is our busy season and the number of special events and festivals we offer will ensure that no matter when you visit, there will always be something fun and exciting to do, including the Father’s Day Car Show held in Hyannis every June, and the Taylor-Bray Farm’s Spring Sheep Festival, held mid-June in Yarmouthport, so it can still be considered spring even though it is past Memorial Day. These Cape Cod events will bring your vacation experiences to the next level of wow, and when you choose our Pretty Picky Properties Cape escapes, in any town, the experience will be heightened even more. Reserve your favorite summer sanctuary today and discover that yes, vacation dreams do come true when those dreams revolve around Cape Cod life!

Cape Cod might be famous for its beaches, seafood shacks, and charming lighthouses, but there’s so much more to experience beyond the postcard-perfect scenes. If you think you’ve seen it all, it’s time to take a closer look. The Cape has a creative, quirky side full of unexpected activities and attractions on Cape Cod that you probably didn’t plan for, but definitely should.

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Lavender Fields and Quiet Trails

Start with a visit to the Cape Cod Lavender Farm in Harwich. It feels like a hidden gem, tucked away off a quiet road, but when the fields are in bloom, it’s absolutely stunning. Even if you don’t catch the peak of the lavender season, the peaceful atmosphere, little woodland trails, and charming gift shop make it worth a stop. It’s a side of Cape Cod that’s slower, softer, and totally relaxing.

Unconventional Museums with Big Personality

Then there’s the Edward Gorey House in Yarmouth Port. If you’re into dark humor, gothic art, or just something out of the ordinary, this place is a must. The late illustrator and author Edward Gorey lived here, and the home has been turned into a museum that reflects his eccentric style. It’s weird in the best way and gives you a deeper appreciation for Cape Cod’s artistic roots.

Seal Watching by Boat

Another under-the-radar experience is taking a seal tour out of Chatham. Most people come for whale watching, but the seal cruises offer something more laid-back and just as memorable. The boat ride itself is beautiful, and watching dozens of seals lounging on sandbars or bobbing in the waves feels like discovering a secret part of the coast. It’s a great option for families, photographers, or anyone who wants to be out on the water without committing to a longer trip.

Gardens, History, and a Carousel

Over in Sandwich, the Heritage Museums & Gardens is another spot people often overlook. Sure, it’s got gorgeous grounds and walking paths, but it also has a classic car collection, a working carousel, and exhibits that change with the seasons. The gardens are especially peaceful in the morning, and the mix of history, art, and nature creates a perfect way to spend a few slow hours. It’s educational without feeling like a chore, and fun for all ages.

Cranberry Bogs and Local Flavor

If you’re into food, check out a cranberry bog tour. Cape Cod is one of the largest cranberry-growing regions in the country, and visiting a working bog is both fascinating and delicious. Some farms offer walking tours or even harvest experiences where you can suit up and step into the bog yourself. It’s hands-on, totally unique, and gives you bragging rights you won’t get from eating another lobster roll.

A Bit of Glass and a Lot of Charm

And if you’re the type who enjoys odd roadside attractions, don’t miss the Sandwich Glass Museum. It may not sound like much at first, but the live glass-blowing demonstrations are genuinely impressive, and the museum’s mix of art, history, and craft is surprisingly engaging. It’s an easy detour that adds a bit of unexpected sparkle to your itinerary.

Find Your Home Away from Home

After a full day of exploring more offbeat attractions on Cape Cod, you’ll want a place to relax and recharge. That’s where we come in. At Pretty Picky Properties, we offer a wide range of vacation rentals to suit any group size. Whether you’re visiting with a small or large group, we have the perfect rental for you. Our properties are located throughout the Cape, from Yarmouth to Brewster, Dennis, and beyond, so you’re never far from where you want to be.

We make it easy to find a home that matches your style. Browse rentals with waterfront views, private pools, hot tubs, pet-friendly features, and more. These homes are designed to help you slow down, settle in, and really enjoy your time on the Cape. Whether you’re returning from a day of kayaking or kicking back after touring a bog, your Pretty Picky rental is where the best parts of the day come together.

Book Your Cape Cod Adventure Today

Cape Cod has a reputation for its quiet charm and coastal beauty, but that doesn’t mean it has to be predictable. There are always new corners to discover, oddities to enjoy, and small adventures waiting just off the beaten path. Contact Pretty Picky Properties today to book your vacation rental!

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The 4th of July on Cape Cod isn’t complete without a hometown parade. Whether you find yourself in Chatham, Orleans, or Centerville, you’ll be treated to colorful floats, lively bands, and plenty of family-friendly fun. If you’re visiting this summer, here’s where you’ll want to be when the celebrations kick off.

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Chatham’s Historic Tradition

Chatham’s Fourth of July Parade is a piece of American history. Known as one of the oldest parades in the United States, Chatham’s parade has been a proud tradition for over a century. This year, the parade kicks off at 9:30 AM, and you’ll want to arrive early to grab a good spot along Main Street. Locals and visitors alike line the streets, many dressed in red, white, and blue, waving flags and cheering as the floats, bands, and performers pass by.

The charm of the Chatham parade is in its authenticity. You won’t find over-the-top commercial displays here. Instead, you’ll see creative homemade floats, veterans riding proudly in convertibles, kids tossing candy, and community groups showing off their local pride. It’s a perfect blend of heartfelt patriotism and lighthearted fun. If you have young kids, they’ll love the lively energy and festive spirit that runs through the whole morning.

Celebrating in Orleans

Just a short drive away, Orleans hosts its own Fourth of July Parade, starting at 10:00 AM. The parade begins at Eldredge Parkway and winds through town before ending at the NRMS parking lot, where judges wait to hand out awards for the best floats and performances. The Orleans parade has a slightly bigger feel while still keeping that classic Cape Cod warmth.

The community spirit in Orleans is truly contagious. You’ll see local businesses, fire departments, youth sports teams, and bands all coming together to put on a colorful and energetic show. Kids often decorate their bikes and wagons, and everyone seems to join in the fun, waving flags and wearing their most spirited outfits. After the parade, families often stroll around town, grabbing ice cream or enjoying a casual lunch at one of the nearby cafés.

Centerville’s Family Fun

Centerville’s Independence Day Parade feels like stepping back in time in the best way. It’s a true community celebration that brings everyone together for a full morning of fun. Things get started early, with children gathering at Centerville Elementary School at 9:00 AM, followed by the parade itself kicking off at 10:00 AM.

The route takes the parade down Bay Lane, onto Bumps River Road, Park Avenue, Main Street, and finally ends at the Centerville Recreation Center. After the parade, the real fun begins. The Centerville Civic Association hosts a post-parade party with grilled hot dogs, cold drinks, and ice cream. There are old-fashioned field games organized by Boy Scout Troop 54, including sack races, field bowling, a candy scavenger hunt, and musical chairs. Face painting by local volunteers is a favorite with the little ones, and there’s even a contest for best costume, best float, best bike, and the much-anticipated ugliest dog competition.

Stay Close to the Fun with Pretty Picky Properties

When you’re spending the Fourth of July on Cape Cod, having the right place to stay makes all the difference. Pretty Picky Properties offers a wide variety of vacation rentals to make your holiday as easy and memorable as possible. Whether you’re traveling solo, coming with the whole extended family, or gathering with a group of friends, there’s a rental that fits your needs.

Our portfolio includes properties across Brewster, Chatham, Orleans, Dennis, Centerville, and beyond. Whether you want pet-friendly accommodations, a pool for relaxing after a long day of festivities, or a waterfront home where you can wake up to ocean views, we have you covered. Each home is hand-selected to ensure a comfortable, stylish, and convenient base for your Cape Cod adventures.

Booking early is always a good idea for the Fourth of July week, but even if you’re planning later, our team is here to help you find the perfect fit. You’ll be close to the parades, the beaches, and all the other activities that make Cape Cod a top summer destination.

Make This 4th of July on Cape Cod One to Remember

Make this Fourth of July one to remember on Cape Cod. From parades to beach days, it all starts with the right place to stay. Book your holiday rental today with Pretty Picky Properties and enjoy a Cape getaway you won’t forget!

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Summer in Cape Cod is a favorite for families, and it’s easy to see why. With its charming towns, calm beaches, and a mix of outdoor adventures and hands-on learning, it’s the kind of place where kids can explore freely and parents can relax. Whether your family loves nature, history, or just good old-fashioned fun, Cape Cod delivers.​

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Beach Days and Tidal Treasures

Cape Cod’s beaches are a dream for families. The bay-side beaches, like those in Brewster, are especially great for younger kids. At low tide, the water recedes to reveal tide pools teeming with hermit crabs and tiny sea creatures, perfect for little explorers. The gentle waves and warm, shallow waters make it easy for kids to splash and play safely. It’s the kind of place where hours slip by building sandcastles, chasing crabs, and collecting shells.​

Outdoor Adventures and Nature Walks

For families who love the outdoors, Cape Cod offers plenty of trails and wildlife. The Cape Cod Museum of Natural History in Brewster is a great starting point. It features interactive exhibits and nature trails that wind through marshes and woodlands, offering a chance to spot birds and learn about local ecosystems. Another gem is the Wellfleet Bay Wildlife Sanctuary, where kids can explore salt marshes, woodlands, and tidal flats, and even participate in programs about local wildlife.​

Hands-On Learning and Play

Cape Cod is rich in opportunities for kids to learn while having fun. The Cape Cod Children’s Museum in Mashpee offers a variety of interactive exhibits designed to spark curiosity and creativity. For a mix of history and play, the Heritage Museums & Gardens in Sandwich features beautiful gardens, a vintage carousel, and Hidden Hollow, an outdoor discovery area where kids can climb, build, and explore.​

Classic Cape Cod Fun

No trip to Cape Cod is complete without some classic family fun. Mini-golf courses are scattered throughout the Cape, each with its own unique theme and challenges. Places like Pirate’s Cove in South Yarmouth and Skull Island in Yarmouth are favorites among families. For a bit of nostalgia, catch a movie at the Wellfleet Drive-In, one of the few remaining drive-in theaters in the country.​

Book Your Family-Friendly Rental with Pretty Picky Properties

After a day of exploring beaches, nature trails, and local attractions, having a comfortable space to come home to makes all the difference. Pretty Picky Properties offers a wide selection of vacation rentals designed to make your Cape Cod stay easy, relaxing, and perfect for the whole family. From roomy homes with multiple bedrooms to cozy cottages by the water, our rentals give you more than just a place to sleep. You get the space to spread out, unwind, and enjoy the time together without the hassle of squeezing into a small hotel room. With full kitchens, private outdoor areas, and plenty of living space, it’s easy to settle in and make yourselves at home.

We offer rentals across Cape Cod in some of the area’s most popular and family-friendly towns, including Brewster, Chatham, Dennis, and more. Whether you want to be steps from the beach or tucked away on a quiet street, there’s a property that fits your style. Some of our homes come with private pools, game rooms, or fire pits, while others are located right on the water with incredible views. Pet-friendly options are also available, so your four-legged family members don’t have to miss out on the trip. Every home is well maintained, clean, and thoughtfully stocked with everything you need to feel comfortable from the moment you arrive.

What makes Pretty Picky Properties different is how personal we make the experience. We don’t just hand you a key, we help you choose the right home, in the right location, with the right features for your family’s needs. Whether you’re traveling with toddlers, teens, grandparents, or a mix of all three, we’ll help you find a place that checks every box. When your rental feels just right, the rest of the trip falls into place.

Create Lasting Memories on Cape Cod

Cape Cod is more than just a summer destination; it’s a place where families come together to create lasting memories. From exploring nature trails and building sandcastles to enjoying local attractions and relaxing in your vacation rental, every day offers something special. So, pack your bags, gather the family, and get ready for an unforgettable summer in Cape Cod!

As you begin to explore all the towns and villages that comprise Cape Cod, you may find yourself drawn to the town of Dennis, offering the feel of a seaside resort and a history that dates back to 1639 when it was first settled. Also home to many of our beautiful and welcoming Cape Cod escapes at Pretty Picky Properties, visitors who decide that Dennis is where their journey is going to bring them can also experience the comforts, luxuries, and special amenities our Dennis retreats will offer. This ultimate Cape Cod guide to Dennis will give you an in-depth look at the places you can visit, the restaurants you will enjoy, and the comfortable adventures you will discover when you come home to our Cape Cod retreats every night of your stay.

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The Villages of Dennis

There are several villages that make up the town of Dennis, each offering its own personality, attractions, and restaurants, and our Pretty Picky Properties are located in or near every village, so no matter where you are exploring, you will never be far from home. Because each of the villages offer something different, we are going to examine each one, giving you tips on the best attractions, restaurants, and in some cases, the fun events that make visitors feel as if they are one of the locals when they attend.

Dennis the Village, AKA North Dennis

Although Dennis was once a part of Yarmouth, it has developed quite a reputation of being a popular spot for tourists to visit, offering a little bit of everything that reflects the lifestyle of Cape Cod, with the activities listed below being the most notable.

Cape Playhouse, 820 Main Street

If all the world’s a stage, Dennis has long been the setting for summer theater, earning a place in history as America’s longest running summer theater. Also known as “the place where Broadway goes to summer,” some of the world’s most famous stage actors have played their part in the performances that have taken place every summer since 1927. Julie Andrews, Henry Ford, and Betty White have all taken a bow on the famous stage of the playhouse, and your summer getaway to Dennis wouldn’t be the same without viewing at least one show.

Mayflower Beach

Considered one of the most beautiful beaches on Cape Cod, its calm waters, brilliant white sand, and family friendly vibe also makes Mayflower Beach one of the Cape’s most popular. Swimming, skimboarding, and beach volleyball are some of the most popular activities here, as well as sunbathing and relaxing, but families with children who are always curious about life and its variety of creatures will appreciate the stories that the tide pools tell.

Sesuit Harbor Café, 357 Sesuit Neck Road & Fin, 800 Main Street

Located on opposite ends of the dining spectrum, Sesuit Harbor Café & Fin offer unique and authentic Cape Cod dining experiences. Sesuit Harbor Café offers a celebration of the classic Cape Cod restaurant, serving up “chowdah,” lobster rolls, and platters of freshly harvested seafood that will ensure you don’t leave hungry. It does not have a liquor license, but you are invited to BYOB, so no sacrifices will need to be made. Fin, however, is a fine dining establishment, located inside an antique captain’s home, offering a glimpse into history as well as an elevated seafood menu that is also locally harvested.

Dennis Port

Once known for its shipbuilding prowess, Dennis Port is also an artist’s colony, an architectural wonder, and one of the first places in the nation to manufacture salt, adding to its mystique and charm.

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Hydrangea House Gift Shop, 227 Depot Street

For as long as there have been flowers on Cape Cod, hydrangeas have grown here, making them an iconic part of the Cape Cod experience, and the Hydrangea House Gift Shop capitalizes on their colorful beauty. Framed by gardens of, you guessed it, colorful hydrangeas, the building in which all manner of hydrangea themed gifts and art is sold is an 1861 Greek Revival Home that is worth a visit even if it didn’t have any gifts inside! Also purchased as part of a larger plan to create an artist’s colony, this female owned business is a wonderful addition to the shopping landscape of Dennis Port.

Sea Street Beach in Dennis Port

There are actually two Sea Street Beaches in the area. One is in East Dennis, located on the bay side; the one we are talking about now is actually in Dennis Port, overlooking Nantucket Sound. Offering lifeguards during the high season and a large parking lot, this is not the beach for people with mobility problems because the only way to reach its powdery sands is by climbing one of two tall staircases.

The Ocean House Restaurant, 425 Old Wharf Road

Whether you are celebrating a milestone birthday or anniversary or are just celebrating the best vacation you have ever taken, a dinner at the Ocean House Restaurant will make your celebration shine bright. This special occasion restaurant is open seasonally, offering a beach bar that overlooks Nantucket Sound and a fantastic menu filled with surf, turf, and Asian specialties and will become an integral part of your celebration.

East Dennis

Quiet and relaxing, East Dennis is the ideal place to visit when you don’t want to deal with the crowds of tourists that can be found in many other Cape Cod towns and villages. A smaller village, you may end up spending more of your time exploring the amenities of our Pretty Picky Properties Dennis retreats, but you may also find yourself enjoying a day on Sea Street Beach, (Remember, there are two Sea Street Beaches!) savoring the serenity that permeates every sea activity or enjoying a fabulous meal at Grumpy’s, located at 1408 Main Street. Open daily for breakfast and lunch, some might go as far as to say if you don’t experience a breakfast at Grumpy’s at least once during your getaway, you will be questioned on the authenticity of your entire Cape Cod vacation experience! Every meal is wonderful at Grumpy’s, but you might want to turn your attention to their Eggs Benedict menu, offering nine different variations that all deserve to be devoured; we love their seafood cake benedict, and their eggplant spinach roasted peppers benny is sure to delight your taste buds!

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South Dennis

Although Dennis is known for its stunning beaches, South Dennis is the only village that doesn’t offer direct ocean access. Some people may consider that a problem, but because all the villages are so close to each other in Dennis, you won’t have far to roam before finding your own stretch of beach on which you can work on your tan, splash around in the surf, and go beach combing for shells and sea glass. (Have you seen some of the art pieces artists are making from sea glass?)

Devil’s Purse Brewing Company, 120 Great Western Road

In our minds there are many wonderful ways to enjoy a summer’s day on Cape Cod, and Devil’s Purse Brewing Company in South Dennis is definitely one of those ways. Closed on Mondays and Tuesdays and offering a beer patio that will allow you to celebrate the season with beers brewed on the premises, including Handline Kolsch, which was originally brewed in Germany but is so much better brewed on this side of the pond. On most days they will sell snacks from food trucks, but if you are here on a day when food trucks aren’t, you are definitely invited to bring your own snacks. Also offering special events that include Lobster Donut Popups, live music, and dog bowl painting sessions, we can’t forget to tell you that leashed dogs that are well behaved are invited to join in your adventures in beer.

Scargo Tower, Scargo Hill Road

Scargo Tower is a 30-foot-tall stone tower that sits atop Scargo Hill, offering views that will take your breath away and providing a peaceful spot to relax and watch the sun set. Originally a shorter tower built of wood (the original Scargo Tower was only 28 feet tall), this stone structure and its predecessor were always meant to be observation towers, at one point offering a telescope that allowed visitors to explore the area even closer. Scargo Tower as it stands today was renovated in 2019, ensuring that your climbing adventures will be safe ones!

Lost Dog Pub, 1374 MA-134

We have always believed that pizza is the international language of love, and although Cape Cod is known for its seafood, we sincerely hope that our South Dennis guests will sample the pizza offerings found at the Lost Dog Pub. Offering a menu that does include a wonderful selection of seafood that is tasty and locally sourced, we hope that you try their pizza at least once, and if you crave seafood but also want pizza, their surf & turf pizza will never let you down. Created with garlic, olive oil, scallops, bacon, and mozzarella, one bite of this special pie and you will be hooked for life!

Cold Storage Beach, 66 Salt Works Road

Parking for Cold Storage Beach is for residents only, but if you want to enjoy a beach experience without venturing too far from home, ensuring that you will make memories you won’t ever forget. Known for its calm waters and for offering the ideal spot to watch all the boats coming in and out of Sesuit Harbor or at the very least, swim, frolic, and search for seashells and colorful sea glass. Dogs are allowed on Cold Storage Beach during the off season, which can be a fun experience for pups that have never played in the sea.

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A Peek into Comfort

Choosing Pretty Picky Properties for your Dennis vacation accommodations is the easy choice, but you might have a little bit of difficulty narrowing your selection down to just one. Our properties are designed to make your traveling to Cape Cod experiences luxurious ones, comfortable ones, and ones that you will never forget, and as you spend your daylight hours exploring Cape Cod, coming home to our homes will add another element of wonderful to your getaway.

Our Dennis retreats, found in the villages that make up this beautiful town, are family homes offering as many as 5 bedrooms and an equal (or higher) number of baths. The kitchens will be spacious and equipped with updated appliances and room for the kids to sit at the breakfast eating a bowl of cereal. Living rooms will be furnished with what we like to call nappable couches (you know what we mean), and more often than not will feature stone fireplaces (it can still get chilly in the summer months) and state of the art televisions. These properties may be located in the middle of town or on the sandy shores of our Dennis beaches, and every moment you spend inside will be ones that you cherish.

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Family Experiences and Traveling to Cape Cod

The amenities we offer outside will enhance your family vacation experience, perhaps enticing you to pencil in at least one day to play at home. From the colorful hydrangea gardens that bloom cheerfully in large backyards to crystal-clear swimming pools, bubbling hot tubs, and firepits that will warm up your nights, these outdoor spaces are an oasis of fun. Barbecue grills, dining tables, lounging spaces, and the occasional outdoor game; all of these extras work together to give you the idyllic Cape Cod vacation experience you deserve! Some of our properties may even feature indoor game rooms or maybe just a pool table set up in an open space, offering you more ways to play. Every attention is paid to every detail when you choose Pretty Picky Properties for your Dennis vacation accommodations.

Come Home to Comfort Every Night of Your Stay

Reserve your favorite Cape Cod escape today and start preparing yourself for a vacation that will remind you dreams really can come true!

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The town of Barnstable (pronounced BARN-stuh-bul in case you were wondering) is the largest town on Cape Cod and is also one of the oldest towns, offering a history that dates back almost 400 years, well before our nation became an independent one. Today, the town is known for its seven villages, its vibrant personality, and for being home to some of the finest Cape Cod escapes from Pretty Picky Properties, offering the chance to live the classic Cape Cod lifestyle while also experiencing luxury that you may not find anywhere else. We want our guests to feel comfortable and at home, not just when residing under the roofs of our Barnstable retreats, but while exploring all this beautiful town has to offer, and as such, we have created this ultimate Cape Cod travel guide to the town, ensuring that you will discover everything you want to see, do, or taste, simply by scrolling down the page!

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The Seven Villages of Barnstable

The villages of Barnstable each reflect a charm and personality all their own and are destined to where your favorite adventures will take place. Below we have listed a little bit about each village, offering a peek into all the ways a Barnstable vacation on Cape Cod will bring you a joy you may not expect to enjoy. Additionally, we will also provide a glimpse into the rentals we may offer in each village, giving you a clearer idea as to what you may expect from your vacation experience. We may not offer properties in every village, but we can assure you that the ones we do will be close enough that you will be able to explore all that Barnstable has to offer, without having to spend all your time traveling from place to place!

Barnstable Village and West Barnstable

It can be confusing when you have a town, a village, and a county all named Barnstable and perhaps even more confusing learning that Barnstable Village and West Barnstable are two separate and distinct entities, but we will talk about the differences below.

Barnstable Village

Barnstable Village is the oldest of the seven villages, and its history makes it one of the more popular of the seven villages. Home to one of the oldest colonial buildings in the country, the Sturgis Library, located at 3090 Main Street, was built in 1644 and today is still fostering literacy, curiosity, and the hunger for learning in all who visit. Barnstable Village is also where the Barnstable Comedy Club has been entertaining guests since 1922. Located at 3171 Main Street and open from November through June, the plays and musicals performed here add light to a dark winter’s night.

West Barnstable

Offering perhaps the most dramatic beach on Cape Cod, Sandy Neck Beach is one of West Barnstable’s biggest claims to fame, stretching out for 8 miles on Cape Cod Bay. The beach and the protected 8000-acre Great Marsh offer the best place to watch the blue heron, for those who are into that sort of thing, but for most, spending the day on soft sands, frolicking in the surf will be your favorite adventure. Or will it be? Luke’s Love Boundless Playground, located at 2377 Meetinghouse Way Route 149 in West Barnstable, is a special place, having been designed to allow children of all physical abilities a place to play and offering play structures that have been created to include options for the wheelchair bound as well.

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Our Properties in These Villages

The homes we offer in Barnstable Village and West Barnstable range in size, but all will offer the comfort you need, the luxury you crave, and all the extras that make vacation travel your favorite thing to do. Spend your days exploring Cape Cod, devouring delicious food, and come home to these spacious abodes to relax and revel in family nights spent playing board games, watching movies on state of the art televisions, and simply sitting out on the back patios, watching the sun set and the moon rise.

Centerville

Although it is Brewster that is known as the Ship Captain’s Town, Centerville, so named for its location in the center of Barnstable, could share this title, once serving as the hometown to many wealthy ship’s captains. Many of their homes still stand today, including “The Captain’s House,” which is located directly across the street from the Centerville Historical Museum on Main Street, and although there aren’t any tours offered, you can still see it when visiting the museum.

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Craigville Beach

Known for being calm and warm, Craigville Beach is one of the most popular beaches in the area, and we advise our guests to plan on spending at least one day swimming, boating, even hunting for shells and sea glass while savoring the serenity of the sea.

1856 Country Store, 555 Main Street

The building of the 1856 Country Store begun its life as a building in which cranberries were stored all the way back in 1840, but it has served as a local general store since 1856 and today is where visitors can buy gifts, souvenirs, and penny candy. Its history makes it a popular stop for tourists, and although we can’t say your visit to Centerville wouldn’t be complete without stopping in, we CAN say it will be a fun place to explore, and you might be sorry if you skipped it.

Four Seas Ice Cream, 360 S Main Street

Visitors and residents have been savoring the frosty treats served at Four Seas Ice Cream since an old blacksmith shop was transformed into an ice cream shop in 1934. Today, a visit to Four Seas is an iconic Cape Cod activity, and this shop is now the oldest continually run ice cream parlor in the entire state of Massachusetts.

Pretty Picky Properties in Centerville

Our Centerville properties are larger ones, designed to handle the needs of big traveling groups with charm, grace, and style. Offering luxury amenities that may include pools, firepits, and enclosed porches, your time spent in our Centerville escapes will be comfortable and filled with fun!

Cotuit (Pronounced kə-TOO-it)

The village of Cotuit is a quiet and peaceful one, known more for its family oriented activities and pristine beaches than for being a tourist destination. Oregon Beach is probably our favorite beach in this town, offering stunning views of Nantucket Sound and providing a more secluded and wonderfully private beach experience for beach goers. The world famous Cotuit oysters come from this town, with the Cotuit Oyster Company dating back to 1857 farming the unique sea treats known for their complex and briny taste. If oysters are a favorite of yours, you may want to time your visit to coincide with the Cotuit Oyster Festival, held in late September. Offering live music and seafood of all types, including their world famous oysters, this fun local event celebrates the return to quiet that takes place after the summer high season has ended. Our Pretty Picky Properties homes in Cotuit are family homes, providing beautiful places to retire to at the end of a long day of Cape Cod adventures and may include outdoor kitchens, swimming pools, game rooms, and so much more!

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Hyannis

Hyannis is the largest village of Barnstable and is also the most well-known, having been the playground for the Kennedys for many decades. It is home to the JFK Memorial and the JFK Museum, one paying homage to our late president and the other offering a peek into his life both in the Oval Office and out of it. The Kennedys are no stranger to Cape Cod, still flocking to our doorstep every July 4th for their traditional holiday celebration, and one of the more exciting parts of a vacation here may be catching sight of a Kennedy “in the wild.” If you want to eat like a Kennedy during your time in Hyannis, Baxter’s Wharf, located at 177 Pleasant Street, has long been a favorite of the Kennedys, inviting locals and visitors to enjoy a casual seafood dining experience since 1957. Offering indoor and outdoor seating, views of the water, and quite possibly a Kennedy sighting or two, their seafood menu is locally sourced and features a local favorite, stuffed quahog, a type of clam.

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Your Hyannis Sanctuary

Hyannis has always been about family, and our properties in this village reflect that family friendly vibe. You probably consider your fur baby a part of your family, and in some of our escapes, you will be invited to bring your sweet pooch along for the ride, as pets may be considered in the property you choose. Unlike many modern homes, our Hyannis properties offer a more traditional floor plan, with each room having its own separate space, adding to their charm and quite possibly, your delight in your choice. Bathtubs may be deep inspiring leisurely soaks, fireplaces may be woodburning, and the views may burrow their way into your heart, ensuring that you will never forget the special moments you enjoyed in our Hyannis retreats on Cape Cod!

Marstons Mills

Marstons Mills is a smaller village, and we wouldn’t be surprised to learn that it isn’t a town you were aware existed. Known for its lakes, cranberry bogs, and ponds, this village located further inland does not provide saltwater beaches, which may be why it is so quiet. Named after the founder of the village, William Marston, and the mills that he owned and operated. The house he once lived in was built in 1744 and has been on the National Register of Historic Places since 1987. Golfers love Marstons Mills, however, as it is the site of the Olde Barnstable Fairgrounds Golf Course, a private course that also welcomes the public. The Tavern on the Green at Olde Barnstable is its 19th hole, offering stunning views of its two courses, as well as serving delicious food and beverages. At the time of this writing, it is under renovation, so you may want to check and see if it is open when your Barnstable journey begins.

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Pretty Picky Properties in Marstons Mills

It is one of the smaller villages, which will mean we may not offer a large selection of properties in Marstons Mills, but we assure you that the ones we do offer will be everything you dreamed they could be. Also family homes, the one you choose may provide wide front porches lined with chairs for optimal neighborhood viewing, swimming pools and firepits in the backyard, and the most nappable sofas on Cape Cod in the living rooms. A good night’s sleep is assured in bedrooms dominated by beds topped with premium mattresses, and multiple bathrooms will help ease morning traffic jams when your entire family is trying to get ready at the same time.

Osterville

The final village of Barnstable, Osterville, offers a long and rich history, having been settled all the way back in 1648. Often described as a seafaring village, its residents were sea captains, cranberry farmers, oyster workers, and shipbuilders and was known as Cotacheset until 1815. Its downtown area is a wonderful place to shop and dine, featuring a surprisingly large number of boutiques, galleries, and eateries, and if your journey brings you to the village in July, you will be able to experience Osterville Village Days, offering a parade, road race, sidewalk sales, and a long list of event activities, all designed to make visitors feel right at home.

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Five Bays Bistro, located at 825 Main Street is one of our favorite restaurants in town, offering a special occasion vibe and an elevated menu filled with surf, turf, and desserts! Our Osterville properties offer everything you have come to expect from Pretty Picky Properties and probably more than you ever dreamed a Cape Cod escape could provide, including swimming pools, modern kitchens equipped with high end appliances, and tranquil settings that will encourage you to relax and forget all about your real world troubles.

Choose our Cape Cod Travel Guide and our Properties for Your Barnstable Retreat

No matter where you are visiting in Barnstable, you will find we are there, offering spacious and inviting homes in all the villages, including Cape Cod visitors guide. Reserve your favorite escape today!

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Looking for the perfect destination to kick off summer this Memorial Day? Cape Cod offers a mix of scenic beauty, charming towns, and exciting activities that make it a top choice for a long weekend getaway. Whether you’re looking to relax on the beach, explore local history, or enjoy some delicious seafood, Cape Cod has something for everyone. Here’s a look at some of the top activities you can enjoy for Memorial Day on Cape Cod in 2025.

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Spend a Day at the Beach

No trip to Cape Cod is complete without spending some quality time at the beach, and Memorial Day weekend is the perfect time to soak up the sun. Cape Cod’s shoreline is dotted with stunning beaches that cater to every kind of beachgoer. Coast Guard Beach in Eastham is a favorite for families, thanks to its wide stretches of sand and gentle waves that make it ideal for swimming. For a quieter, more relaxed vibe, Mayflower Beach in Dennis offers soft white sand and calm waters, making it perfect for families with young kids.

If you’re feeling adventurous, head to Nauset Beach in Orleans, where you can surf or take a long walk along the shore. For those looking to unwind, pack a picnic and spend the afternoon lounging by the water while enjoying time outdoors.

Explore Historic Provincetown

If you’re looking for a dose of history and charm, Provincetown should be at the top of your list. Located at the tip of the Cape, Provincetown is rich in history and culture, offering a vibrant mix of art galleries, unique shops, and delicious dining options. Start your visit by climbing the iconic Pilgrim Monument, where you’ll be rewarded with panoramic views of the harbor and surrounding area.

Stroll along Commercial Street, where you can explore eclectic boutiques, sample local treats, and soak in the lively atmosphere. For art enthusiasts, Provincetown’s thriving art scene is worth exploring, with numerous galleries showcasing works by local and international artists. If you’re traveling with family, take a whale-watching tour from the harbor, where you’ll have the chance to see whales up close.

Savor Fresh Seafood

One of the highlights of any visit to Cape Cod is indulging in fresh, local seafood. Memorial Day weekend is the perfect time to treat yourself to classic New England favorites like lobster rolls, clam chowder, and fried clams. For a casual dining experience, stop by one of the many seafood shacks that dot the coastline. Sesuit Harbor Café in Dennis is a local favorite where you can enjoy a lobster roll while overlooking the water.

For a more refined dining experience, consider visiting one of Cape Cod’s renowned seafood restaurants. Enjoy waterfront dining at places like The Ocean House in Dennis or Chatham Bars Inn in Chatham, where you can enjoy freshly caught seafood while taking in stunning views.

Take a Bike Ride

If you’re in the mood for some outdoor adventure, the Cape Cod Rail Trail offers a scenic and enjoyable way to explore the area. Stretching for 25 miles through picturesque towns and woodlands, the trail is perfect for both casual cyclists and more experienced riders.

Start your ride in Dennis and make your way through charming towns like Harwich, Orleans, and Eastham. Along the way, you’ll pass cranberry bogs, salt marshes, and serene lakes, making it a great way to connect with nature. Stop at one of the local cafes or ice cream shops along the trail to refuel before continuing your journey.

If biking isn’t your thing, many sections of the trail are also perfect for walking or jogging, giving you the opportunity to take in the beauty of Cape Cod at your own pace.

Book Your Memorial Day Rental with Pretty Picky Properties

When it’s time to choose the perfect place to stay for your Memorial Day getaway, Pretty Picky Properties offers a wide selection of stunning vacation rentals across Cape Cod. Whether you’re looking for a waterfront home in Chatham, a cozy pet-friendly cottage in Dennis, or a luxurious property with a private pool in Yarmouth, we have something for every group size and preference.

Our rentals are designed to make your stay as comfortable and memorable as possible. Many of our properties feature fully equipped kitchens, spacious outdoor areas for family gatherings, and amenities like hot tubs and game rooms to keep everyone entertained. We also offer a variety of pet-friendly rentals, so you don’t have to leave your furry friends behind.

Make Your Memorial Day on Cape Cod Unforgettable

Cape Cod is the perfect destination to celebrate Memorial Day in 2025. Whether you’re lounging on the beach, exploring historic Provincetown, or enjoying fresh seafood with loved ones, there’s something for everyone. Book your Memorial Day rental with Pretty Picky Properties today!

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The history of Chatham goes way beyond the year it was incorporated (1712, in case you were wondering) with its landscape and salt ponds being created by glacial action during the last Ice Age, creating the beauty you will be exploring during your Cape Cod journey. Offering historical sites, tranquil beaches, and the world-famous Chatham Lighthouse, the time you spend in this town will only get better when you choose Pretty Picky Properties for your vacation accommodations. Reflecting the beauty and charm of Chatham, our homes and cottages will welcome every travelers, creating a safe space filled with all the comforts of home. This guide to things to do in Chatham will show you more about the town and about all you can expect from our Chatham escapes.

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Something for Everyone

The appeal of our New England town reaches out to everyone who steps within its city limits, and crossing boundaries that you might not expect from a vacation destination. History is all around as you pose for family pictures at the base of the famous Chatham Lighthouse, constructed in the very early years of the 19^th century (1808, to be exact) marvel at the Chatham Windmill, which was once used for grinding corn, and explore the nautical history of Cape Cod at the Chatham Marconi Maritime Center. But Chatham is also a movie making town, its land and seascape having been featured in several movies, including “The Finest Hours” a true story about a famous Coast Guard rescue. And then, on another front, there is the natural side of our Cape Cod hometown, offering warm water beaches, the Monomoy National Wildlife Refuge, and sunsets that will literally take away your ability to speak. A vacation spent in Chatham is destined to be a well rounded one and we’ve listed more of our favorite adventures in more detail in the next paragraphs.

Chatham Railroad Museum, 153 Depot Road, Closed Sundays and Mondays

 Traveling by train used to be one of the few ways you could get to Cape Cod after the construction of the railway bridge, but it was more than just a way to get here, train travel was the source of romance and excitement. Today, we tend to drive or fly everywhere, but when you visit the Chatham Railroad Museum, you may find yourself longing for the romance of those long ago days. Housed in a former railway depot, the museum has long been a favored attraction, opening its doors in 1960, and the structure itself was placed on the National Register of Historic Places in 1978. Its impeccably restored 1910 caboose is probably our favorite exhibit of all, allowing visitors to step inside and see for themselves what the romance of train travel was all about.

Families Love Us

 In addition to the Chatham Railroad Museum, there is a large amount of Chatham, Cape Cod things to do with families that will appeal to all age groups, activities which include, of course, toes in the sand time. There are many beaches in Chatham in which you can frolic in the surf and build sandcastles at water’s edge, but perhaps the best known one is Lighthouse Beach, lying in the shadow of, yes, you guessed it, the Chatham Lighthouse. It’s white sands are soft and stunning, framing deep blue waters perfectly, and when the sun is setting behind the Chatham Lighthouse, well, we dare you not to fall in love. We’ve listed more family friendly activities below.

AWSC Shark Center Chatham, 235 Orleans Road in North Chatham

Sharks have fascinated us for years and the AWSC Shark Center in Chatham will make your children excited about learning. Offering a selection of water tours that explore the world beneath the waters while educating travelers about sharks and their importance in the earth continuum.

Chatham Candy Manor, 484 Main Street in Chatham, Open Daily 10-6

Do not even try to tell us candy is just for kids, or if you really think that way, we invite you to walk inside the Chatham Candy Manor and spend a little time there. We’re pretty sure it won’t take long to change your mind forever as you scope out all the delicious treats found under its roof, including seasonal collections that offer fun treats such as candies that look like mummies, bats, and pumpkins at Halloween. Featuring small batch fudge that will melt your heart, hand dipped chocolates, truffles, creams, and caramels, and they even offer sugar free sweets that don’t taste sugar free at all.

Chatham Orpheum Theater, 637 Main Street in Chatham

Rainy days and lazy days are always the best times to see a movie and although you can choose to stream movies on our large televisions and stay comfy and cozy as the rain drums down on the roof overhead, the Chatham Orpheum Theater offers fun things to do in Chatham. Offering artsy films and special events, kid’s movies, and classic movies that you will thrill to see on the big screen. Also offering a concession stand that includes pizza, wings, sandwiches, and a host of ice cream treats, honestly, hanging out at the Orpheum is one of our favorite things to do any time of the year.

Cause for Celebration

Just like in your own hometown, the holidays are a time for celebration and the special events listed below celebrate many of the bigger holidays with local celebrations that offer an all-American small town charm and appeal.

4^th of July Parade

While parades seem to be disappearing from the national landscape, the Chatham 4^th of July Parade is an event we look forward to every year. Offering a different theme each year (in 2024 the theme was Chatham-It’s a Shore Thing!) there will be colorful floats, classic cars, fire trucks, and fishing boats and a vibe of cheer and happiness that will definitely make you feel proud to be an American.

Pumpkin People in the Park at Halloween

Also offering trick-or-treating and costume parties, the Pumpkin People in the Park event is not as spooky as it sounds and is a lot of fun! Chatham has been listed as America’s 4^th best town for Halloween and the pumpkins that are made to look like people are one of the top reasons. Kate Gould Park is the “scene of the crime,” and the pumpkins are sure to make you laugh.

Christmas Stroll in Chatham

As you can imagine, Christmas on Cape Cod already looks like a scene straight off a Christmas card, but you may not be able to imagine it gets even better with the Christmas Stroll in Chatham. The shops on Main Street are decorated in colorful lights that shimmer against a blanket of snow that is on the ground, Santa makes an appearance at the fish pier, candy canes are being made, carriage rides are being taken, and of course, people are strolling around in their winter warmest clothes, enjoying every single second of this festival.

Naturally Beautiful

The natural side of Chatham offers its own charms and is guaranteed to make every picture you take appear as if a professional has taken it. It is nearly impossible to take a bad picture outside in Chatham and these outdoor Chatham, Cape Cod things to do will give you a peek into the serene, tranquil, and a little bit of the wild side of our Cape Cod hometown.

Monomoy National Wildlife Refuge, 30 Wikis Way

There are eight different refuges that make up the Eastern Massachusetts National Wildlife Refuge Complex, and the Monomoy National Wildlife Refuge is one of those important eight. Protecting the wildlife that inhabit its nearly 8000 acres, including migratory birds, gray seals, and horseshoe crabs and as you explore its paths and walkways, you will learn just how much each of the creatures are important to the life we lead, even if we can’t see them on a regular basis.

Beachcomber Boat Tours, 174 Crowell Road

Some of the most beautiful parts of Chatham are on the water and Beachcomber Boat Tours let’s travelers explore that part of our world. Offering seal tours along the Chatham Waterways, the Beachcomber is known for its banana color and shape, taking tourists to the places where the seal’s play and the scenery takes their breath away. Private charters are offered and many of the happiest people we have ever met have been married aboard one of the company’s larger boats, witnessed by friends, family, and of course, Beachcomber staff.

Kate Gould Park, 15 Chatham Bars Avenue

A walk in the park, in Kate Gould Park to be more precise, is destined to be a favorite activity, even if you aren’t visiting while the pumpkin people are residing there. Offering a classic gazebo which is where Friday concerts are held in the summer months and all generations of family members dance and sing along to the tunes being played, this park isn’t one you go to have a picnic or to play on a playground, but it is the centerpiece to almost every event that takes place in Chatham, giving visitors a better chance of learning the town a little better.

Follow the Scent of Our Best Restaurants

The best vacations often revolve around the meals we devour and our Chatham restaurants are sure to give you stories to tell, all good ones of course, and the restaurants listed below are a great start to your taste tour of Cape Cod.

Chatham Filling Station, 75 Old Harbor Road

 The Chatham Filling Station is not a gas station, it is one of our favorite brunch spots, their brunches are so good they serve it all day! Closed on Wednesdays and Thursdays, the menu is filled with all your favorite breakfast foods, including their Station Breakfast Sandwich and an extensive Benedict section. This wonderful restaurant offers the best way to start your day and can also be a great lunch spot as well.

Wild Goose Tavern, 512 Main Street, Open Daily at 11:30

Speaking of lunch, colorful murals on the walls of the Wild Goose Tavern remind us that life isn’t meant to be serious all the time, especially the one with the geese bellying up to the bar. Offering a little of this, a little of that, and a lot of seafood dishes, the convivial vibe, delicious foods, and creative cocktails will make this eatery one of your favorites and you may even find yourself going back for dinner.

The Chatham Squire, 487 Main Street, Open 11:30 to 1 AM Daily

Whether you are coming to the Chatham Squire for lunch, dinner, or drinks and entertainment, the Chatham Squire will not let you down. Also offering a Sunday brunch, the Squire has been a local tradition since 1958 and if you come all this way and don’t visit the Chatham Squire, can you really feel you have explored all Chatham has to offer? This local hot spot is one we highly recommend at Pretty Picky Properties.

Come Home to Chatham and Our Pretty Picky Properties Retreats

No matter how you fill the minutes of your dream vacation in Chatham, coming home to our Pretty Picky Properties vacation retreats will provide the perfect ending to each beautiful day. Offering all the comforts of home, guests can choose rentals that provide as many as eight bedrooms, giving each traveler their own space to retreat to when the moon is high in the sky and as few as two bedrooms, for those more intimate escapes to the Cape. We pay attention to all the details that make vacation life comfortable and easy and there will be lobster pots in the kitchens, and because we understand the importance of having fun, there may even be game rooms, theater rooms, swimming pools, and hot tubs for your entertainment purposes!

Check Out Our Chatham Luxury Rentals Here!

Every Chatham Adventure Begins and Ends with Pretty Picky Properties

Reserve your favorite Chatham retreat today and be prepared to be the envy of all your friends, family, and acquaintances that weren’t able to accompany you on this trip of a lifetime!