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!
Browse our Yarmouth Vacation Rentals Here!
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!
