11 best things to do on Martha’s Vineyard

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Playful yet elegant, Martha’s Vineyard has an aura like no other island. Get ready for picture-perfect beaches and towns brimming with opportunities to create unforgettable vacation memories. Here are our must-dos, taking you to the heart of the experience.

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What to expect when visiting Martha’s Vineyard

Martha’s Vineyard is one of those true summer colonies. The Massachusetts island swells with spring, booms during summer and retreats back to its quieter self as the first autumn winds arrive.

But even at summer’s peak, you find that appreciated peace on Martha’s Vineyard. With a size of almost 100 square miles, it’s the third largest island on the East Coast of the USA.

Down-Island is the more concentrated part of the island, where you find its three major towns. These centers, filled with fun things to do, are Edgartown, Oak Bluffs and Vineyard Haven.

Up-Island is the slice of Martha’s Vineyard that keeps incredibly quiet even during summer. Here, the tiny West Tisbury, Chilmark and Aquinnah are excellent spots when you crave for solitude.

It might seem like an eccentric, and excessively overplayed, joke. However, the Down-Island hubs line up along Martha’s Vineyard’s northern shore, while the Up-Island gems appear across the island.

The background is that the terms “Down-Island” and “Up-Island” live on from the early whaling days of Martha’s Vineyard. As you travel Up-Island, which rather means west than north, the longitude coordinate goes up.

1. Tour Wesleyan Grove

The Wesleyan Grove district in Oak Bluffs undeniably grabs your attention. Its streets are lined by more than 300 gingerbread cottages, which in radiant colors appear like rainbows.

These iconic Carpenter Gothic structures, centered around a tabernacle, go back to the 1860s and 1870s. Then, they were built primarily for religious summer camps.

For its mark on history, the entire Wesleyan Grove district is recognized as a National Historic Landmark.

Stroll around the gingerbread cottage area steeped in tradition, and, if you can, pick a favorite facade. Although much has changed since the colorful houses were built, they continue to add character to Martha’s Vineyard.

Purple gingerbread house with white touches and a porch equipped with a bench and chairs in Wesleyan Grove on Martha's Vineyard
Oak Bluffs gingerbread cottages.

2. Walk down Circuit Avenue

Just steps from Wesleyan Grove, another highlight is Circuit Avenue. It’s the main drag in Oak Bluffs.

Grab some seafood, have a refreshing drink or just enjoy the pleasant ambience as you stroll towards the waterfront. There, the Oak Bluffs Fishing Pier welcomes new island visitors.

Want to stay right at the action of Oak Bluffs? The Oak Bluffs Inn, with a signature front porch, sits conveniently on Circuit Avenue.

3. Take a spin on Flying Horses

An Oak Bluffs attraction appreciated by young and old, the Flying Horses Carousel is not your typical amusement park carousel. Built in 1876, it’s America’s oldest platform carousel offering one-of-a-kind rides.

Take a spin on the Flying Horses and feel the nostalgia. Made of wood and with manes and tails of real horsehair, these horses spent a few years on Coney Island but have been in Oak Bluffs since 1884.

On top of the vintage charm, there’s a fun bonus feature.

While the merry music-playing carousel goes around, the riders reach out to grab rings. If you manage to catch a brass ring, you have won yourself a free Flying Horses ride — and some eternal Martha’s Vineyard respect.

4. Find peace at Ocean Park

Near the liveliness of Circuit Avenue, and the ferry terminal, you find a peaceful oasis. Oak Bluffs’ iconic Ocean Park is the perfect spot when you need to catch a break.

Just its open space of green grass and ocean views make Ocean Park a favorite place to kick back. Other beautiful features are the centerpiece gazebo and surrounding Victorian house facades.

People relaxing on the green lawns of Ocean Park, Martha's Vineyard, decorated with a waving USA flag
Ocean Park in Oak Bluffs.

5. Explore Edgartown Historic District

Each town on Martha’s Vineyard has its own charm. Edgartown, the island’s easternmost town, boasts a streetscape as elegant as it is historic.

Edgartown’s heart, listed on the National Register of Historic Places, contains hundreds of historic ship captain’s homes in Greek Revival style. Most of these structures were built in the 1800s when Martha’s Vineyard was a whaling center.

On top of the good looks, there’s the bubbling commercial activity.

6. Browse Main Street

How about two for one? Main Street is the celebrated road that ties Edgartown Historic District together.

On Main Street, lined by historic ship captain’s homes, you find old-school restaurants, easy-going bars and cute independent shops. It’s Edgartown’s quintessential hub of activity.

In this area, you also find several of the best Edgartown hotels. The Richard not only offers elegance but also sits with the best of Main Street within steps.

Blue hydrangeas in front of white house with green shutters in Edgartown, Martha's Vineyard
Edgartown in bloom.

7. Venture to Chappy

Chappaquiddick Island, or just Chappy, is located at the eastern end of Martha’s Vineyard. As sand banks sometimes connect the two, but other times don’t, Chappy is a so called “occasional island”.

Regardless if Chappy is connected or not, it’s a separate world out there. On the untouched island, nature comes first, second and third.

Here, in the secluded setting, hiking, biking and relaxing are popular activities.

From Edgartown to Chappaquiddick Island, it’s just a few hundred feet with the Chappy ferry. Even though the lines tend to get long in summer, the ride itself takes less than five minutes.

8. Photograph Edgartown Lighthouse

Martha’s Vineyard, like the rest of coastal New England, has a special relation to its lighthouses. These man-made structures proudly guard the island, fitting into the landscape like if they always have been there.

From east to west, Martha’s Vineyard is home to: Cape Poge Lighthouse, Edgartown Lighthouse, East Chop Lighthouse, West Chop Lighthouse and Gay Head Lighthouse.

Which Martha’s Vineyard lighthouse that’s the best one? That’s up to each observer to decide.

However, one of the most visited lighthouses is Edgartown Lighthouse. Marking the entrance to Edgartown Harbor, it’s also an attraction that’s easily accessible.

White Edgartown Harbor Lighthouse and benches where visitors can sit down to enjoy the ocean view
The lighthouse in Edgartown.

9. Lounge by Jaws Bridge

Beach Road is an iconic Martha’s Vineyard drive. Connecting Oak Bluffs with Edgartown, it highlights the beauty of the island’s northern coastline.

About halfway from Oak Bluffs to Edgartown, Jaws Bridge (officially titled the American Legion Memorial Bridge) is more than a bridge.

This spot features in the 1975 Jaws movie, considered the first real summer blockbuster ever. In Jaws, the island is called “Amity Island”, but that island really is Martha’s Vineyard.

Just the coastal surroundings make driving Beach Road a gorgeous thing to do. Still, the Hollywood fame and your own personal recognition add a dimension to the Jaws Bridge drive.

10. Get to know Vineyard Haven

Oak Bluffs has its gingerbread cottages, while Edgartown presents ship captain’s home after ship captain’s home. With that in mind, it’s not so strange that Vineyard Haven gets fewer headlines.

But the third Down-Island town is the real gateway to Martha’s Vineyard.

Vineyard Haven is the only island town with a year-round ferry service. With that comes appreciated activity every month of the year.

On Main Street in Vineyard Haven (don’t confuse it with Edgartown’s Main Street), establishments of all kinds lure you in. If you’re after a unique Martha’s Vineyard souvenir, this is a great spot to secure it.

11. Conquer Aquinnah Cliffs

Yes, you find many of the best things to do on Martha’s Vineyard in the Down-Island area. However, if you look for serenity, nothing beats a day trip to the Up-Island area.

When you go from east to west, you in order encounter West Tisbury, Chilmark and Aquinnah. They have in common that they are tiny towns with few attractions and distractions.

Yet that quitness is exactly why the Up-Island area is so loved.

At its westernmost point, the Aquinnah Cliffs tower up, offering superb Atlantic views. The Aquinnah Cliffs, where Gay Head Lighthouse stands, is the awe-inspiring ending that Martha’s Vineyard deserves.

Red Gay Head Lighthouse protruding from the lush vegetation at Aquinnah Cliffs
Gay Head Lighthouse.

Where to stay

Awesome, now you know what to do on Martha’s Vineyard. But which are the best Martha’s Vineyard areas and hotels?

For the full experience, including effortless access to restaurants, shops and attractions, don’t look past the Down-Island area. Oak Bluffs and Edgartown are for good reasons the most popular towns on the island.

Down-Island is, although at least as pretty as the rest of the island, further away from most things to do. However, it’s the prime Martha’s Vineyard area if you look for solitude.

Pequot Hotel – Beach-ready lodging

Martha’s Vineyard has a special bond to the ocean. Positioned right by the beach, Pequot Hotel beautifully celebrates that. How about a late night beach walk or a swim before breakfast?

The Richard – Endless fun

Right on Main Street in Edgartown, the Richard makes it easy to enjoy the best things to do on Martha’s Vineyard. Add to that uniquely styled rooms and an inviting garden where you happily lounge, preferably with a cold one in your hand, throughout the afternoon and evening.

Harbor View Hotel – Upscale Martha’s Vineyard

Want to feel true luxury when visiting Martha’s Vineyard? If so, the roads lead you to Harbor View Hotel. Overlooking Edgartown Lighthouse, the hotel is upscale yet offers those homey New England touches.

Houses behind dune-vegetation overlooking uncrowded beach on Martha's Vineyard
Hit the beach on Martha’s Vineyard.

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