Cape Cod is different from many other vacation destinations, and part of that is due to how it governs itself. Divided into 15 self-governing towns, each with its own series of villages, it is also divided into four distinctly different regions: Upper, Mid, Lower, and Outer Cape. Today, we at Pretty Picky Properties are going to take you on a tour of the towns on Cape Cod (and their villages as well) and offer a peek into the properties we offer in each area.
Understanding the Cape’s Regions from Upper Cape to Outer Cape
Another thing that is different about Cape Cod is the way we have named its different areas. Instead of using traditional map terms, we use sailing terms: the Upper Cape is closest to the mainland, and the Outer Cape is at its northernmost tip. The villages on Cape Cod will be associated with the towns and share their vibe while maintaining their own personalities. And no matter where you stay, the area’s history will keep you in a constant state of awe, while our retreats will keep you feeling welcome and at home.
Outer Cape: Provincetown, Truro, Wellfleet, and Eastham
Provincetown, Truro, Wellfleet, and Eastham are towns on Cape Cod, located in the Outer Cape. The Outer Cape is where our nation’s history began, as it is the area known for being the first landing place of the pilgrims.
- Browse our Outer Cape vacation rentals
Provincetown
Our first town on Cape Cod is Provincetown. Not many people know this, but Provincetown is where the pilgrims landed first, dropping anchor in Provincetown Harbor in 1620. Today, the tallest granite structure in the US stands 252 feet tall and proud, and is a popular spot for tourists. Provincetown is also famous as an LGBTQ+ vacation destination, offering a vibrant arts and dining scene. Race Point Beach faces the Atlantic Ocean, offering large waves, dramatic sunset views, and a large seal population. The Lobster Pot on Commercial Street is an iconic Provincetown restaurant, featuring a stupendous lobster-centric menu and a history spanning decades.
Truro
Cape Cod’s oldest and most powerful lighthouse, Highland Light, can be found in Truro. Offering a casual and unpretentious vibe, famous painter Edward Hopper painted what we think was some of his best work right here. And because Truro is also home to Cape Cod’s oldest winery, Truro Vineyards, you have to know we are going to suggest you drop in for a tasting or risk not truly experiencing the heart of this beautiful town on Cape Cod.
Wellfleet
Wellfleet’s biggest claim to fame is its extensive oyster farms, and its oysters have played a big part in history, having once been the star attraction in the White House when John F. Kennedy was President of the United States. Marconi Beach is perhaps its best-known beach, named after Italian inventor Guglielmo Marconi, as the Marconi Wireless Station was where the first two-way message was sent. The Beachcomber in Wellfleet is the most iconic restaurant in this town on Cape Cod, serving seafood in a historic 1872 lifesaving station.
Eastham
Although Provincetown is our first town, Eastham is known as the “Gateway to Cape Cod.” This is where the Cape Cod National Seashore starts and where Miles Standish and his scouting party first encountered our native residents. First Encounter Beach, located at the end of Samoset Street, marks this historic meeting with a commemorative plaque that was designed to look like part of the sand.
The oldest working windmill, the Eastham Windmill, built in 1680, can be found at 2515 Mid-Cape Highway and is definitely worth a visit. Finally, when you are craving the deliciousness of a classic Cape Cod seafood dinner, we must recommend Caroline’s Bar & Grill (4380 US-6). Open weekdays at 4 PM and at noon for lunch on Friday’s and Saturdays, this reasonably priced eatery is relatively new to the North Eastham landscape, but its seafood menu (splurge for the lobster dinner!) has fast become our favorite.
Lower Cape: Brewster, Chatham, Orleans, and Harwich
Moving on to the Lower Cape, this is where you will find Brewster, Chatham, Orleans, and Harwich.
- Browse our Lower Cape vacation rentals
Brewster
We aren’t supposed to call favorites, but Brewster is, and has always been where we call home, with our main office residing within the town limits. And although you will find Pretty Picky Properties retreats in nearly every town on Cape Cod, we do offer the largest selection of homes in Brewster. Brewster is “the Sea Captains’ Town,” offering 50+ mansions previously owned by local sea captains.
The Cobb House Museum (739 Lower Road) is the former home of Captain Elijah Cobb. It is open for tours on Thursday, Friday, and Saturday from 1 PM to 4 PM and offers a fascinating peek into the lives of 18th century sea captains. This area is also known for the herring runs that happen every spring in Stony Brook, the Brewster Flats (tide pools and sandbars), and our favorite May festival, Brewster in Bloom. The Brewster Fish House (2208 Main Street), a favorite of locals for over 40 years, is destined to offer you your favorite meal of your vacation. Try the Pappardelle; you can thank us later!
Chatham
Chatham is home to four villages on Cape Cod, the famous (and still operational) Chatham Light, and is also the site of our country’s first organized tree planting. Erosion was once a major issue in Chatham, so in 1821, pine trees and beach grass were planted to help stop erosion and keep its villages from being buried in sand. Today, it’s a beautiful and relaxing place to visit, and in June 2026, Chatham Light reopened after being closed for a couple of years for repairs. We highly recommend you take a tour. The Impudent Oyster is a popular dining spot, located inside what was once a local church and offering an elevated seafood menu. Ducks in the Window is a quirky shop in Chatham selling nothing but rubber ducks in all colors and sizes.
Orleans
Our next stop on the Cape is at a town with a strong military history, being the only town struck by gunfire during WWII. It is also the only town on Cape Cod with a French name, Orleans, named in gratitude for the Duc’ d’Orleans and for France’s help during the American Revolution. Rock Harbor Beach is where Lifeboat CG36500 is docked; it was featured in the Disney movie, The Finest Hours. Instead of a restaurant, we suggest you visit Hot Chocolate Sparrow, a local coffee shop famous for its rich, sweet hot chocolates. (Their coffee and sweet treats aren’t so bad either!)
Harwich
There are seven villages of Cape Cod in Harwich, a town famous for its cranberry bogs. Yes, the commercials you have seen are realistic portrayals of cranberry bogs (even though they were filmed in Wisconsin, not Cape Cod). A tour of the bogs is highly recommended. For dining, we’re going to skip seafood and head to one of Harwich’s villages, Harwich Port, for a visit to George’s Pizza. George’s is a much-loved landmark, having served more than its fair share of Greek-style pizzas, pastas, and subs for over 55 years, making it our top pick for food during your stay.
Mid-Cape: Hyannis, Yarmouth, and Dennis
The Mid-Cape area is known as the heart of Cape Cod, includes Hyannis (Barnstable), Yarmouth, and Dennis.
- Browse our Mid-Cape vacation rentals
Hyannis
Known for years as the “summer White House,” Hyannis is home to the Kennedy compound and the museum celebrating his life. The John F. Kennedy Hyannis Museum is filled to the brim with artifacts about our 35th President, and a visit to his museum is well worth the trip. The HyArts Cultural District is the first cultural district on Cape Cod, and the studios here showcase the best artists in the country. Thriving, bustling, and vibrant, Hyannis offers a big city vibe while also serving as a windsurfing paradise. Baxter’s Boathouse, once a Kennedy family favorite, has been a local landmark since 1967 and is still one of our favorite seafood eateries.
Yarmouth
Yarmouth is one of the oldest towns on Cape Cod, incorporated in 1639, over 100 years before we celebrated our independence as a country. It’s pirating history, however, may attract families; the Whydah Pirate Museum, located in West Yarmouth, offers genuine pirate treasure for your perusal. Also known for its 18th-century windmill (the Judah Baker Windmill) and for 45 years, Capt. Parker’s Pub has served yummy comfort food, including its award-winning New England clam chowder.
Dennis
Dennis’s vibe is summer fun and laidback wonder. We love Dennis any time of year, of course, but a huge reason for its summer vibe is that it is home to our nation’s oldest summer theater, the Cape Playhouse. There’s something wonderful about watching a performance on a stage that once featured the superstars of Hollywood, including Bette Davis and Julie Andrews, and we hope you add a visit to your itinerary. Tidal flats bring their own beauty to this charming town, with Mayflower Beach providing a low tide adventure you will never forget. Finally, Ocean Restaurant was named one of America’s top 100 restaurants, offering an elevated menu that serves a little bit of everything, including tapas choices, steaks, and seafood.
Upper Cape: Falmouth (Woods Hole), Mashpee, and Sandwich
As we near the end of our exploration of the towns on Cape Cod, it is time to discover all that the Upper Cape has to offer. The entire Upper Cape has a vibe grounded in community and history, making it a popular part of the island for history buffs and families.
Falmouth
Falmouth is perhaps the town that best represents Cape Cod, offering energy and history that excite all visitors. Falmouth’s vibrant, bustling downtown area inspires strong devotion from tourists and residents. Unlike other towns, Falmouth has a strong year-round population with residents loving every minute of their life on Cape Cod. This leads to fewer seasonal shutdowns of restaurants and shops, which means that no matter when you visit, you can explore the seafood specialties at The Quarterdeck.
Woods Hole (Part of Falmouth)
Home to the Woods Hole Oceanographic Institution, which played a role in the discovery of the Titanic wreck, Woods Hole also boasts the nation’s oldest aquarium. History and nature go hand in hand here, and whether you are a fan of the quirky (a house made with the wings of a WWII airplane or a house with a ship built into it) or are simply looking for a quiet and restful escape from real life, Woods Hole appeals to many types of people. Pie in the Sky Bakery on Water Street is our top recommendation for dining in the village, offering sweet pastries you will crave forever.
Mashpee
Drawing from its extensive Native American history, Mashpee (an Anglicization of a native name, meaning “great water”) celebrates uniqueness. It is home to the Mashpee Wampanoag tribal headquarters, and when America is celebrating 4th of July, Mashpee offers a three-day powwow, hosting Wampanoag Tribe members from all over the world.
Much of the land in this town is protected, and Cape Cod’s smallest schoolhouse, the 1831 Schoolhouse, is open for tours. There is no traditional downtown, but life centers around the Mashpee Commons, which is where the elegant and upscale Bleu Restaurant is located. This lovely French restaurant is the perfect date night spot, offering an authentic menu (including escargots)!
Sandwich
History buffs may want to choose Sandwich as their favorite town on Cape Cod, as it happens to be the oldest town! Sandwich was settled all the way back in 1637 and is also home to the oldest house on Cape Cod, Hoxie House, built in 1675. There are many things to see and do in this wonderful town with 4 different villages, including visits to the Sandwich Glass Museum, the 17th-century Dexter Grist Mill, and the Sandwich Friends Meetinghouse, the oldest Quaker meetinghouse in America. The town features 7 public swimming beaches, including 4 saltwater ocean beaches, with Town Neck Beach perhaps being the most recognizable, offering the iconic Sandwich Boardwalk. Watching your meal get unloaded from the boats at Fishermen’s View Restaurant (they boast the freshest seafood in the state) is a local tradition that brings the phrase “boat to table” into play.
Book a Vacation Rental Near Your Favorite Town or Village
Hopefully, this study of the towns on Cape Cod will make your decision about where to stay much easier. Pretty Picky Properties offers rentals in most of the towns featured here and in many more as well. Reserve your favorite retreat today!
