17 Fun Things to Do in Martha’s Vineyard, Plus Where to Eat and Stay

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Menemsha Harbor in Winter Martha Vineyard
Located on Martha’s Vineyard, Menemsha Harbor glows at sunset. Photo credit: Massachusetts of Travel and Tourism

Martha’s Vineyard is like a Jennifer Weiner beach read come to life. The picturesque island, just south of Cape Cod, Massachusetts — and a hop, skip and jump away from Boston, New York and other East Coast cities — oozes New England charm. Even better, there are plenty of fun things to do in Martha’s Vineyard to keep everyone entertained.

Accessible solely by boat or air, it’s known for its breezy spirit and Americana charm — think gingerbread cottages, picket fences draped in plump hydrangeas, beautiful beaches, scenic lighthouses, quaint harbor towns and farmstands.

This Massachusetts island has also long been known as a vacation haven for the rich and/or famous, including former US presidents John F. Kennedy, Bill Clinton and Barack Obama and celebrities such as Oprah Winfrey, Michael J. Fox, Spike Lee and Carly Simon.

What makes visiting Martha’s Vineyard so attractive – aside from its natural beauty – is its abundance of sightseeing, shopping and outdoor activities. You’ll find everything:  bike rides, hiking trails, kayaking, birding, beach hopping, fishing and golfing.

It’s an ideal summer getaway – summer is peak season. But it’s just as attractive in fall and spring when Martha’s Vineyard is quieter and far less crowded.

But where to start? This 87-square-mile island is made up of six towns: Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury and West Tisbury. Each has its own character and array of activities.

17 Must-See Spots in Martha’s Vineyard

1. Explore Oak Bluffs

As this is where the ferry pulls in, Oak Bluffs will most likely be your first introduction to Martha’s Vineyard. Circuit Avenue is where you’ll find an abundance of shops and restaurants including the ever-popular ice cream and dessert shops Mad Martha’s Ice Cream, Back Door Donuts and Ben & Bill’s Chocolate Emporium of Martha’s Vineyard.

Oak Bluffs is also where you’ll find The African-American Heritage Trail of Martha’s Vineyard, which traces (and honors) the island’s Black history.

2. Ride the Flying Horses Carousel

Go back in time – and enjoy what’s billed as “the nation’s oldest platform carousel.” Made in 1876 by the toymaker Charles Dare, the delightful Americana relic features 20 hand-painted wooden horses with glass eyes and real horsehair. There are also four chariots, all fastened to a rotating platform.

Check the hours before you go. If you’re there between May 31 and June 17, you can enjoy a free tour.

3. Visit the Gingerbread Cottages

Oak Bluffs is home to one of the island’s most photographed spots. Known as Cottage City, this neighborhood is an assortment of rainbow-hued gingerbread cottages built in 1835 when a group of local Methodists used to attend religious camp meetings in Oak Bluffs.

Their storybook look, complete with front porches and in many cases, rockers, is an Instagram dream. It’s also historic as Oak Bluffs was one of the first places African Americans could escape to enjoy a beach vacation. The Shearer Cottage in particular has a rich history.

4. Bike Ride

The best way to see the island – and its numerous towns – is to see it from two wheels. There are more than 40 miles of bike trails that go from Vineyard Haven to Oak Bluffs to Edgartown. The trails are flat for the most part, meaning they work well for families, as well as adults who may not want the extra exertion!

For advanced riders, West Tisbury, Chilmark and Aquinnah have more challenging, hilly and curvy terrain. Download this bike map from the Martha’s Vineyard Commission.

Didn’t bring your bike? No worries. There are many bike rental companies, a majority of which are clustered near the Vineyard Haven ferry terminal and the seasonal terminals in Oak Bluffs and Edgartown.

View of cliffs and lighthouse overlooking the ocean at Martha's Vineyard, one of the beaches in Massachusetts.
Panorama of a Gay Head lighthouse on a cliff in Aquinnah, Martha’s Vineyard. Photo credit: Shutterstock

5. Beach It

The beautiful beaches are one of the main reasons to vacation here and Martha’s Vineyard has a large variety, from secluded spots to more expansive stretches. The only caveat: Some are open to the public while others are reserved for residents and summer visitors staying in specific towns.

Keep in mind, you may need a parking and or town beach permit. The Martha’s Vineyard Chamber of Commerce has a full list of beaches including news about restrictions on dogs (many beaches do not allow them, particularly in the summer).

Facing the Atlantic Ocean — and open to all — is Katama Beach in Edgartown, on the South Side, known for its large waves, while Edgartown Beach in Edgartown gets rave reviews for its calm, clear waters.

“Jaws” fans will want to check out Joseph Sylvia State Beach, along the the Nantucket Sound shoreline in Edgartown and Oak Bluffs, as this is where filming took place.

Public beaches are East Beach, Fuller Street Beach, Eastville Beach, Oak Bluffs Town Beach, Lake Tashmoo Town Beach, Owen Park Beach and Tisbury Town Beach.

Off-limits is the endangered Gay Head Cliffs and beach. But they can be seen from Moshup Beach via a short walking trail.

6. Look for a Lighthouse

Martha’s Vineyard is a treasure trove of lighthouses, most of which you can visit seasonally. There are five in total, each with its own maritime history.

The West Chop Lighthouse, at the entrance of Vineyard Haven Harbor, dates to 1817 and was moved from a bluff to avoid slipping away to sea. It’s the only one not open to the public.

The East Chop Lighthouse, which also dates to the 1800s, is located in Oak Bluffs. This is where the first telegraph signals were sent. The other three are the Gay Head Lighthouse, which overlooks Aquinnah’s red clay cliffs; Edgartown Lighthouse and Cape Poge Lighthouse, on Chappaquiddick’s northeast point.

7. Visit the Jaws Bridge

The American Legion Memorial Bridge on Beach Road connecting Edgartown and Oak Bluffs is where “Jaws” was filmed, giving it the unofficial Jaws Bridge title.

Though the movie came out in the 1970s, the bridge remains a “must see” attraction. It’s also popular for the many kids (and adults) who jump off it each summer into the water below.

8. Tour Chappaquiddick Island

Chappaquiddick is infamous because of the 1969 car accident involving the late Massachusetts Senator Ted Kennedy that took the life of Mary Jo Kopechne, a former campaign aide to Robert Kennedy.

The island — a ferry ride away and a great day trip for those staying in Oak Bluffs, Edgartown, Vineyard Haven, Aquinnah, Chilmark, Tisbury or West Tisbury — is popular for its natural beauty. Plus, it’s home to the still operational Cape Poge Lighthouse, also in “Jaws,” and the Cape Poge Wildlife Refuge, known for its expansive salt marsh and salt pond.

Sightseeing in Chappaquiddick should also include a visit to Wasque Nature Reserve and Mytoi, a 14-acre Japanese garden filled with native and exotic plants.

9. Say “Ahh’ at The Aquinnah Cliffs

These stunning red clay cliffs, carved by glaciers millions of years ago, are located on the southern coast of Martha’s Vineyard. They are one of the island’s most popular – and dramatic — spots. Warning. The parking lot fills up fast so you may want to bike here or take a tour bus.

10. Go ‘Green’ at the Polly Hill Arboretum

More natural beauty awaits at this 72-acre public garden, developed by the late legendary horticulturist, Polly Hill. Located in West Tisbury  — and on the National Register of Historic Places  —  the arboretum is full of lush rare trees and plants from around the world including gorgeous North Tisbury azaleas.

11. Do Yoga at an Alpaca Farm

Try alpaca yoga at Island Alpaca Company (register to take a class). Or, skip the yoga and enjoy the herd of more than 50 colorful Huacaya alpaca at this alpaca farm. Check the farm’s schedule for shearing days and other events.

12. Visit the Martha’s Vineyard Museum

This historical and cultural museum, located in Vineyard Haven, features art, artifacts, oral histories and more, giving you a thorough history lesson in everything Martha’s Vineyard.

13. Get your Farm Fix at Morning Glory Farm

Martha’s Vineyard has an abundance of farmstands; the family-run Morning Glory Farm, which grows food for the entire island, features a busy farmstand, bakery and kitchen and is open year-round. It’s well-known for its bread, cheese and flowers.

14. Enjoy Nature at Felix Neck Wildlife Sanctuary

Martha’s Vineyard is bursting with wildlife and natural beauty making outdoor activities an easy breezy adventure.

Located in Edgartown, the Felix Neck Wildlife Sanctuary has lots of hiking trails as well as plenty of woodlands, meadows, ponds and salt marshes for exploring.

15. Hike Menemsha Hills

Gorgeous views await at Menemsha Hills in Chilmark where, at the top of Harris Trail, you’ll see the Menemsha Harbor entrance, the Elizabeth Islands and the Gay Head Light lighthouse.

16. Shop

Old fashioned New England charm is alive and well at both The Chilmark General Store in Chilmark (which dates to the early 1900s) and Alley’s General Store in West Tisbury.

Grange Hall in West Tisbury is another blast from the past. Built in 1859 as the center for agriculture and commerce, this historic barn building now hosts a regular farmer’s market on Wednesdays and Saturdays from June through October, as well as art festivals and special events.

Of course there also are plenty of gift shops in Edgartown, Oak Bluffs, and Vineyard Haven. Stick to Main Street and North Water Street in Edgartown where Edgartown Books is a popular spot.

Circuit Avenue in Oak Bluffs is the main drag there while Main Street should be your starting point in Vineyard Haven.

For the ultimate preppy look — which practically screams “I vacationed in Martha’s Vineyard” — head to the Black Dog Dockside Premium Outlet (Dockside Marketplace) in Oaks Bluff or  Vineyard Vines in Vineyard Haven.

17. Eat Lobster Rolls/Have a Clambake

This is a New England must. Luckily, there are numerous places to find this Massachusetts culinary treat, including:

Also worth seeking out: Edgartown Seafood Market in Edgartown where lobster rolls are a top sell and the selection of fish changes daily.

Other Places to Eat:

  • Atlantic Restaurant, Edgartown: An indoor/outdoor venue known for its fresh seafood, steaks and more. However, they don’t take reservations.
  • Mad Martha’s Homemade Ice Cream: Ice cream is practically a Martha’s Vineyard pastime. Luckily this ice cream shop, with homemade flavors like Chilmark Coffee and Dairy-Free Black Raspberry, has locations in Edgartown, Oak Bluffs and Vineyard Haven.
  • 19 Raw Oyster Bar, Edgartown: “Shucking amazing” is the mantra at this raw bar where seafood towers are among the specialties. Also expect lobster tacos, a lobster roll, oyster po’boy, ceviche and more.
  • Lookout Tavern, Oak Bluffs: Located on a bluff overlooking the water, this seafood restaurant, popular for its lobster rolls as well as its sushi, has a great view of incoming and outgoing boats. No reservations.
  • The Black Dog Tavern, Vineyard Haven: The restaurant, with its iconic black dog T-shirts and caps, started here on Martha’s Vineyard, in Vineyard Haven in 1971 as an ode to living life on the seashore with a dog.

Where to Stay

Martha’s Vineyard’s towns – Aquinnah, Chilmark, Edgartown, Oak Bluffs, Tisbury and West Tisbury – offer a variety of accommodations from vacation rentals to hotels and motels to classic New England inns and campgrounds.

The Martha’s Vineyard Lodging Association is one place to scout out lodging and special offers. Possibilities include:

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