Martha’s Vineyard Towns: Historic Charm With Scenic Views

Martha’s Vineyard Towns: Historic Charm With Scenic Views

Martha's Vineyard is one of the most sought-after vacation spots in America. Home to 17,000 year-round residents, this New England island hosts over 200,000 people during the summer months. With its beautiful beaches, quaint towns, and bustling nightlife, Martha's Vineyard has something for everyone to explore.

But which of Martha's Vineyard towns should you visit? Continue reading to learn about each of the six towns on Martha's Vineyard and what activities you can do in each.

The History Martha's Vineyard 

Martha's Vineyard is an island located south of Cape Cod, Massachusetts. The island was originally home to Native American tribes. These tribes go as far back as 2270 B.C.

The Wampanoag people, a.k.a "People of the First Light", originally named the island, Noepe (land amid the waters) and lived there for thousands of years. In 1602, Bartholomew Gosnold renamed the island, Martha's Vineyard. It soon became a popular place for whaling and maritime operations in the 1700s and 1800s.

In 1835, Edgartown Methodists began holding exclusive camp meetings. These meetings are said to have been the catalyst in promoting resort tourism in Martha's Vineyard. Nowadays, this island is home to many powerful people including CEOs, millionaires, and even former President and First Lady Obama.

Martha's Vineyard has two distinct areas, "up-island" and "down-island". Up Island refers to the western rural side of the island. On the western side, you'll find three of the six towns, Aquinnah, Chilmark, and West Tisbury. Down Island refers to the busier eastern side which includes Edgartown, Oak Bluffs, and Vineyard Haven.

Each of the six towns is unique and some even have smaller villages of their own. No matter which Martha's Vinyard town you choose, you'll find the charm of New England in each one.


Edgartown is the oldest community on Martha's Vineyard. Edgartown was originally established in 1642 with the name, "Great Harbor". This town was preferable to whaling captains and the maritime community.

If you're a history buff, you'll love walking down North Water Street. This street is known for its historic homes and architectural landmarks including the Edgartown Lighthouse and the Carnegie.

If you're in the mood to spend the night out, head over to Main Street in Edgartown Square. Main Street is home to many lively bars and restaurants including The Port Hunter and The Wharf.

If you're in the mood to shop till you drop, Main Street is also home to many charming local boutiques. Here, you'll be able to add some summer pieces to your closet or simply purchase a local souvenir for your loved one. The shopping in Edgartown is known as some of the best shopping in all of Martha's Vineyard.

You can also choose to relax at one of the many beaches in Edgartown including South Beach, Lighthouse Beach, Fuller Street Beach, and more!


Katama is a residential area located in Edgartown. Home to beautiful South Beach, Katama is known to be a surfer's paradise. Similar to Edgartown, Katama has walkable cobblestone streets with historical homes and architecture. Katama is just a short 4-mile bike ride from Main Street in Edgartown.


Chappaquiddick, otherwise known as Chappy, is another area just outside of Edgartown. Once attached, Chappy is now only accessible by boat or the town ferry. Chappaquiddick is a rural area with just one paved main road and one store for supplies.

Chappy is a nature lover's paradise. This area has 800-acres of beautiful naturally preserved land.

Oak Bluffs

Oak Bluffs is north of Edgartown and known for its victorian inspired architecture. It is also known for its lively nightlife and miles of beachfront.

While in Oak Bluffs you can take a historical walking tour of the old Methodist camp meetings, also known as Cottage City. You can also visit the nation's oldest continually-operating carousel, located in downtown Oak Bluffs.

Oak Bluffs is known to have one of the best music scenes on Martha's Vineyard. The downtown area is full of bars and restaurants that encourage dancing all night. Or, choose to stop in an ice cream shop and walk along the boat harbor to take in the sunset.

Vineyard Haven

Vineyard Haven, also known as Tisbury, is also located on the eastern side of Martha's Vineyard. The main ferry port is also located here and is open year-round.

Vineyard Haven is known to have a vibrant arts community with many art galleries. Feel free to catch a performance at the Katherine Cornell Theater and Vineyard Playhouse. The Owen Park gazebo is open during the summer for outdoor events. Plus, catch award-winning film festival movies at the Martha's Vineyard Film Center.

The downtown area has a lively nightlife scene with its many bars, shops, and restaurants. Sailing, boating, and kayaking are popular activities on Vineyard Haven's public beaches. There are also many private beaches and waterfront homes located in this area.

West Tisbury

West Tisbury is considered to be an "up-island" town of Martha's Vineyard. In 1892, West Tisbury split from its parent town Tisbury or Vineyard Haven. This area is considered rural but does have a small, charming downtown area.

West Tisbury is home to the famous Alley's General Store. This store is Martha's Vineyard's oldest continually-operating business. You'll also find farmer's markets and local artisan festivals in the downtown area.

This agricultural town has freshwater ponds, rolling farmlands, and winding roads through tree-lined havens. You can also take advantage of beautiful hiking trails, water exploration, bird watching, and bike paths for the outdoor enthusiast.


Chilmark is known to have some of the best scenic views on all of Martha's Vineyard. Chilmark is known for its rolling hills, stone walls, and dramatic coastlines. Here, you can escape the summer crowds for quiet fishing villages and catch sight of sheep grazing on the hills.

Don't be surprised if you have to wait in line at The Bite, the Back Door at Homeport, or Larsen's Fish Market. It will be worth it when you taste the delicious, local seafood!

Chilmark is family-friendly and hosts many events in the summer including the Film Festival with Cinema Circus. You can also hike Prospect Hill, the highest point on the island, and swim at residential beaches.

Chilmark is a great place to visit if you wish to slow down and take in the scenery on your vacation. Walkable streets and a panoramic view of the island's natural beauty make this a unique place in Martha's Vineyard.


Menemsha is the most popular town in Chilmark, known for its fishing village harbor. Menemsha can be a bit busier because of its many small shops, restaurants, and beaches.

Picnicking is a staple in Menemsha. Locals and tourists alike will bring their blankets and picnic baskets along the shore to watch the sunset. After all, Menemsha is also known to have the best sunset view in all of Martha's Vineyard.


Aquinnah is the farthest western town in Martha's Vineyard. It is best known for the colorful Gay Head Cliffs. These cliffs encompass a spectrum of colors including green, yellow, black, brown, red, and white. Atop of these cliffs, you'll also find the Gay Head Lighthouse, a registered national historic landmark. The first federally recognized Native American tribe, the Wampanoag tribe, is also situated here.

There are a few places you can eat in the area. The most popular restaurant is called The Outermost Inn. This restaurant has spectacular views and is often booked far in advance.

Aquinnah is home to many residents and beaches. There are few homes you'll be able to see from the road. Most estates are tucked away to ensure privacy. One famous estate, in particular, is 377-acres and was once owned by former First Lady, Jackie Kennedy.

Aquinnah is a beautiful and luxurious area on Martha's Vineyard. This town encapsulates the island's history, beautiful scenery, and luxurious feel.

Martha's Vineyard Towns

The three towns of Aquinnah, Chilmark, and West Tisbury offer a slower-paced and nature-focused vacation. In these towns, you'll be able to sit back and relax away from the crowds and surrounded by birds and even sheep!

The other three towns of Edgartown, Vineyard Haven, and Oak Bluffs are busier beach towns with lots of shopping, bars, and restaurants to choose from. In these towns, you can dance with friends, buy gifts for your loved ones, and relax on the many public beaches.

Choose which Martha's Vineyard towns you'd like to visit by deciding what is most important for you and/or your loved ones. Are you more "up-island" or "down-island"?

If you're planning on visiting Martha's Vineyard, book your vacation home with us today. With beautiful rooms and plenty of amenities, our rentals are perfect for your next New England getaway!



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Sandy Shores

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