A Cape Cod vacation is destined to be one of the greatest vacation you have ever taken, no matter which community, town, or village you choose to stay in, but there are ones that we at Pretty Picky Properties believe will truly enhance your vacation experience. The sun appears to shine brighter, the beaches seem warmer and more welcoming, and because we refuse to offer anything less than the best for our guests, you will find our Cape Cod vacation retreats luxuriously residing within the city limits. This guide to the top Cape Cod communities will give you a better idea of what to expect and help you to narrow down your final destination to the community that best fits your family’s needs.
Barnstable, Founded in 1639
Barnstable is one of the oldest communities on Cape Cod, steeped in history and offering seven charming villages, many of which we will be discussing further down the page. Home to the Olde Colonial Courthouse built in 1774, making it one of the oldest Colonial buildings in the country, the rich history, stunning views, and natural landscape will ensure that there is always something wonderful to do or see without having to travel far. The best time to visit is (and this will pretty much stay the same for all communities unless otherwise noted) in the months of May, June, September, and October, as the weather will be wonderful, and the crowds will be smaller. We like to call it “Locals Summer”. Below, we have listed some of our favorite Barnstable activities, attractions, and restaurants.
Sandy Neck Beach Park
Offering a 6.5-mile-long barrier beach with dunes that can reach up to 100 feet tall, Sandy Neck Beach Park is popular with hikers, bird watchers, swimmers, and drivers, as the beach can be driven on with offroad vehicles with the proper permit.
Barnstable Comedy Club, 3171 Main Street
Barnstable’s long history means it features a lot of “the oldest” businesses, buildings, etc., and the Barnstable Comedy Club falls under the category of the oldest club in the area. Continually open for over 100 years, talented performers have helped guests lose themselves in the magic on the stage, and that magic continues today.
The Dolphin Restaurant, 3250 Main Street
There’s a reason long running restaurants last, and that reason is a complicated blend of staff, ambience, and of course, good food. The Dolphin Restaurant, in business for over 70 years, is the perfect example. Moderately priced and offering a menu filled with both surf and turf options, we have visited many times over the years and never had a bad experience. Seafood on Cape Cod is fresher and sweeter than what you may be used to, so if you are choosing between a burger and their shrimp and scallops, go for the latter. You can thank us later!
Brewster, Founded in 1803
Brewster is one of the newer Cape Cod areas founded in 1803. It was originally settled in the mid-1600s. Brewster is home to the largest pond on Cape Cod, coincidentally named Long Pond, and is nicknamed the Sea Captain’s Town due to the large number of sea captains who once settled there.
Brewster General Store, 1935 Main Street
Shopping is a popular activity during any vacation, and there is a large selection of stores in the area that we highly recommend, but perhaps the most fascinating one is the Brewster General Store. The building in which the store is housed was originally a church, but in 1866 it was converted into a general store and has been a primary source of candy, gifts, toys, and yummy ice cream ever since.
Stony Brook Grist Mill, 830 Stony Brook Road
Originally built in 1699, the grist mill was washed away in a storm. It was rebuilt on the same site in 1751 using beams from the original building. During the Revolutionary War, grains from the mill were taken to feed British soldiers, and today it is the last remaining building of Factory Village, a once thriving industrial part of Brewster. Open for tours on weekends during the spring and summer months, cornmeal is still made and sold at the mill, providing a unique souvenir for your travels.
Spinnaker Restaurant, 2019 Main Street
Reservations are required for Spinnaker Restaurant, one of our favorite Brewster special occasion eateries. The menu changes on a regular basis, and with each new rendition we grow to love it more, recommending that guests save room for dessert—in particular the chocolate dessert of the day!
Chatham, Incorporated in 1712
Although it wasn’t incorporated until 1712, Chatham was originally settled in 1685. Its charm and beauty stand out in the Cape Cod communities in that is renowned for both, so be sure to keep your camera handy when visiting.
Chatham Lighthouse, 37 Main Street
Constructed in 1808, the Chatham Lighthouse still shines its light over stormy waters today and during the season (July through September). Operating 24 hours a day, it stands 48 feet tall, and fortunately for tired travelers, it takes only 44 steps to reach the top.
Ducks in the Window, 507 Main Street
One of the quirkier stores on Cape Cod, Ducks in the Window is loved by all, as its shelves are filled with rubber ducks of all sizes and professions. Yes, we said professions, as there are police ducks, nurse ducks, even teacher ducks, and you can’t help but smile and be happy when you walk into the store for the first time.
The Chatham Squire, 487 Main Street
The Chatham Squire is a typical New England restaurant, featuring casual décor, a great bar, and good food that sticks to your ribs as you go about your touristy business. The bar side offers video games and foosball, while the dining side is a little more formal, providing a menu filled with seafood delights you will greatly miss when it is time to leave Cape Cod. Meet me at the Squire!
Dennis, Settled in 1639, Incorporated in 1793
The history of Dennis makes it a popular vacation destination for history buffs, offering a large variety of historic neighborhoods that visitors simply love to stroll about in.
The Cape Playhouse, 820 Main Street
Professional summer theater isn’t as big of a deal on the mainland as it once was, but on Cape Cod, it is integral to the Cape Cod experience, and the Cape Playhouse has been continuously running since 1927. Famous for Humphrey Bogart performing on its stage, you will feel a sense of history as you sit in the audience, perhaps imagining what it would have been like to watch the talented Humphrey Bogart performing.
All American Town of Dennis Fireworks
The end of summer is always a sad time for Cape Cod, but the party that sends off our guests with a bang is something to look forward to. Featuring a Hallmark movie style bonfire on the West Dennis Beach, there will be live music, the opportunity to roast marshmallows, and the big burst of colorful explosions in the sky, all guaranteed to make this farewell to summer shine a little brighter.
Grumpy’s, 1408 Main Street in East Dennis
Breakfast is the most important meal of the day, and when you enjoy it at Grumpy’s, we can promise you won’t leave grumpy or unsatisfied. Grumpy’s selection of benedicts boggles the mind, and if you are here long enough, you may want to work your way through each dish.
Harwich, Founded in 1665 and Incorporated in 1694
Cranberry bogs have been a huge part of Cape Cod for over 200 years, with Harwich being the town most commonly associated with the colorful fruit. Harwich has been named as America’s second happiest seaside town.
The Harwich Cranberry Arts & Music Festival, Weekends in September
One of our favorite local festivals, the Harwich Cranberry Arts & Music Festival pays homage to the cranberry with food trucks, live music, and a wooden dance floor in a tent, as well as over 150 craft vendors selling jewelry, art, gifts, and handmade foods. The best way to get to know the area you are visiting is by attending its local festivals, and this end of season festival will bring you joy.
Watch the Harwich Mariners Win a Game
The Cape Cod Baseball League is where tomorrow’s superstars perfect their game, with some of the MLB’s biggest players having hit a homerun with their traditional wooden bats. Thurman Munson, Jason Varitek, Aaron Judge, and many, many more have played on these hallowed fields, and who knows? Maybe the players you are watching today will be tomorrow’s superstars.
Cape Sea Grille, 31 Sea Street in Harwich Port
Housed inside a former sea captain’s home, Cape Sea Grille is a wonderful special occasion spot serving new American cuisine. Open year round and offering elevated selections of surf or turf meals, their braised pork Osso Busco is a dish dreams are made of.
Hyannis Port, Founded in 1639
Hyannis Port has a long history, but perhaps its most famed time were the years the Kennedys made the village their playground. The Kennedy compound has been the summer home for the Kennedys since the 1920s, when Joseph Kennedy first rented the initial cottage for a summer vacation. The family still owns the compound, and the widow of Robert F. Kennedy actually lived there until her death in October of 2024.
John F. Kennedy Hyannis Museum, 397 Main Street in Hyannis
The Kennedy name was much loved in this part of Cape Cod, on all of Cape Cod, and the JFK Hyannis Museum pays proper homage to the hero whose life was cut too short. Hyannis Port was always considered the heart and home of the Kennedys, and the museum doesn’t stop at chronicling JFK’s life but touches on all the Kennedys who lived and loved here through the years.
Baxter’s Wharf Restaurant & Waterfront Dining, 177 Pleasant Street in Hyannis
We can’t help but focus on the Kennedys when discussing Hyannis Port, and we aren’t going to stop with the restaurant suggestion. Baxter’s Wharf Restaurant was known to be where the Kennedys ate often, and if you had visited during that time, chances are you may have dined in the same room as the President, his brother, or any of the numerous family members who made Cape Cod their home in the summer months.
Orleans, Settled in 1693
Orleans is the only US site attacked during WWII, when a German U-boat fired at the tug, Perth Amboy. Today, it is known for its beautiful landscape, arts scene, and its history that began long before the U-boat incident, an incident that Disney made a movie about in 2016.
Jonathan Young Windmill, 41 Old Kings Highway in Orleans
Most people do not know that there are seven windmills on Cape Cod, with the Jonathan Young Windmill being built in the early 18th century. It is a unique part of our history, still offering original parts that actually work. Open to the public in July and August, the windmill took a circuitous route to get to where it stands today, having been built in South Orleans, moved to the center of town, then to Hyannisport, then returned to its current location.
The Alley Bowling & BBQ, 191 MA-6 in Orleans
Combining the fun of candlepin bowling and the yum of house smoked barbecue, the Alley Bowling & BBQ may be your favorite Cape Cod experience of all. Candlepin bowling is played with smaller balls and thinner pins and is a sport that originated right here in New England. Barbecue may not be a food that is unique to Cape Cod, but we assure you that you will find no beef with their beef!
We Are There
The best communities of Cape Cod have one major thing in common: our Pretty Picky Properties are located in each and every one! Offering comfort, style, and a quiet New England luxury, our properties will become an integral part of your vacation experience. Reserve your favorite today!
