Martha’s Vineyardis 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 Yorkand other East Coastcities — oozes New Englandcharm. Even better, there are plenty of fun things to do in Martha’s Vineyardto 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 Massachusettsisland 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 Vineyardso 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 Vineyardis quieter and far less crowded.
But where to start? This 87-square-mileisland 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 Bluffswill 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 creamand dessert shops Mad Martha’s Ice Cream, Back Door Donuts and Ben & Bill’s Chocolate Emporium of Martha’s Vineyard.
Oak Bluffsis 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 Bluffsis home to one of the island’s most photographed spots. Known as Cottage City, this neighborhood is an assortment of rainbow-hued gingerbread cottagesbuilt in 1835 when a group of local Methodistsused to attend religious camp meetingsin 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 Cottagein 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 Havento Oak Bluffsto 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, Chilmarkand Aquinnah have more challenging, hilly and curvy terrain. Download this bike mapfrom the Martha’s VineyardCommission.
Didn’t bring your bike? No worries. There are many bike rental companies, a majority of which are clustered near the Vineyard Havenferry terminal and the seasonal terminals in Oak Bluffsand Edgartown.
5. Beach It
The beautiful beachesare one of the main reasons to vacation here and Martha’s Vineyardhas 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 VineyardChamber of Commerce has a full list of beachesincluding news about restrictions on dogs (many beaches do not allow them, particularly in the summer).
Facing the AtlanticOcean — and open to all — is Katama Beachin Edgartown, on the South Side, known for its large waves, while EdgartownBeach in Edgartowngets rave reviews for its calm, clear waters.
“Jaws” fans will want to check out Joseph Sylvia State Beach, along the the NantucketSound shoreline in Edgartownand Oak Bluffs, as this is where filming took place.
Public beaches are East Beach, Fuller Street Beach, Eastville Beach, Oak BluffsTown Beach, Lake Tashmoo Town Beach, Owen Park Beach and Tisbury Town Beach.
Off-limits is the endangered Gay HeadCliffs and beach. But they can be seen from MoshupBeach via a short walking trail.
6. Look for a Lighthouse
Martha’s Vineyardis 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 HavenHarbor, 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 iswhere the first telegraph signals were sent. The other three are the Gay Head Lighthouse,whichoverlooks Aquinnah’s red clay cliffs; Edgartown Lighthouseand Cape Poge Lighthouse, on Chappaquiddick’s northeast point.
7. Visit the Jaws Bridge
The American Legion Memorial Bridge on Beach Roadconnecting Edgartownand Oak Bluffsis where “Jaws” was filmed, giving it the unofficial Jaws Bridgetitle.
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 MassachusettsSenator 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 tripfor 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 marshand salt pond.
Sightseeingin Chappaquiddickshould also include a visit toWasque Nature Reserveand 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 thesouthern 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 Vineyardhas 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 Vineyardis bursting with wildlife and natural beauty making outdoor activitiesan easy breezy adventure.
Located in Edgartown, the Felix Neck Wildlife Sanctuaryhas lots of hiking trailsas well as plenty of woodlands, meadows, ponds and salt marshesfor exploring.
15. Hike Menemsha Hills
Gorgeous views await at MenemshaHills in Chilmarkwhere, at the top of Harris Trail, you’ll see the MenemshaHarbor entrance, the Elizabeth Islandsand the Gay Head Light lighthouse.
16. Shop
Old fashioned New Englandcharm is alive and well at both The Chilmark General Storein Chilmark(which dates to the early 1900s) andAlley’s General Storein West Tisbury.
Grange Hallin West Tisburyis 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 shopsin Edgartown, Oak Bluffs, and Vineyard Haven. Stick to Main Street and North Water Street in Edgartownwhere Edgartown Booksis a popular spot.
Circuit Avenue in Oak Bluffsis 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 theBlack Dog Dockside Premium Outlet(Dockside Marketplace) in Oaks Bluffor Vineyard Vinesin Vineyard Haven.
17. Eat Lobster Rolls/Have a Clambake
This is a New Englandmust. Luckily, there are numerous places to find this Massachusettsculinary treat, including:
- Menemsha Fish Market in Chilmarkknown for its lobsters, lobster rolls, clam chowder (gluten-free available too!), oysters and steamers
- John’s Fish Marketin Vineyard Havenprovides much of the same, along with fish and chips and lobster salad.
Also worth seeking out: Edgartown Seafood Market in Edgartownwhere lobster rollsare 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 creamis practically a Martha’s Vineyardpastime. Luckily this ice creamshop, with homemade flavors like ChilmarkCoffee and Dairy-Free Black Raspberry, has locations in Edgartown, Oak Bluffsand 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 rollsas 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 Havenin 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 Englandinns and campgrounds.
The Martha’s Vineyard Lodging Associationis one place to scout out lodging and special offers. Possibilities include:
- Harborview Hotel, Edgartown:This popular hotel has long catered to Martha’s Vineyardvisitors.
- Summercamp, Oak Bluffs:Ocean-front hotel with a summer camp vibe.
- The Oak BluffsInn, Oak Bluffs:A wraparound porch and a great downtown location owned by locals make for an ideal spot to start your vacation.
- Vineyard Square Hotel & Suites, Edgartown:A stylish, beachy spot steps away from downtown Edgartownand close to the ferry.
- Winnetu Oceanside Resort, Edgartown:Luxury hotel with a special beach clambake.
