How to Spend Three Days On Martha’s Vineyard, Massachusetts

Lighthouses, quaint towns and amazing seafood await on this coastal island just a few hours away from Boston.

Martha's Vineyard, photo by Daniel Esmaili/500 px

Known as the stand-in for shark-plagued Amity Island in Jaws, and a favoured vacation spot of U.S. presidents such as Ulysses S. Grant and Barack Obama, the island of Martha’s Vineyard is located about three hours south of Boston. Though relatively small—measuring just 42 by 13 kilometres—it’s packed with seaside treats and easily accessible adventures: ride the United States’ oldest merry-go-round, explore glistening barrier beaches and indulge in oysters straight out of the water.


Day 1


After a breakfast of freshly made doughnuts—try the Boston Cream—and coffee at the Gourmet Café and Bakery in Oak Bluffs, take a wander over to the Wesleyan Grove neighbourhood to see the 19th-century “gingerbread cottages,” so-named for their pretty colours and ornate Victorian detailing.


Take a ride on the Flying Horses Carousel, the United States’ oldest merry-go-round, before visiting Mad Martha’s for a sweet treat. This popular spot has been serving homemade ice cream for nearly 50 years. After, head to Joseph Sylvia State Beach to paddleboard or kayak along this barrier beach. Local Island Spirit Kayak offers rentals.


For dinner, drive about 10 minutes from Oak Bluffs to the waterfront Garde East restaurant, located in Vineyard Haven, a community in the town of Tisbury. Order the clambake dinner, which includes lobster, clams, mussels, corn and smoked seaweed. After, catch a film at the restored Capawock Theatre, one of Massachusetts’ oldest still-working cinemas.

The Wesleyan Grove neighbourhood in Oak Bluffs, photos by Jeffrey Silvers/Alamy


Day 2


Start your day with Johnny Cakes topped with maple whipped cream at Behind the Bookstore café in Edgartown. The island’s oldest European settlement, Edgartown is lined with impressive 19th-century houses. Tour the pre-colonial Vincent House Museum on Main Street; built in 1672, it’s the island’s oldest residence.


Lunch harbour-side on fresh oysters at Atlantic Fish & Chop House. Then, hire bikes at adjacent Martha’s Vineyard Bike Rentals before catching the Chappy Ferry (the same one used in Jaws) for the 161-metre “journey” to sparsely populated, shop-free Chappaquiddick Island. Once there, pedal between attractions such as the Cape Poge Wildlife Refuge, Wasque Beach and the Mytoi Japanese Garden.


Back in quaint Edgartown, kick back with a cool beer and charcuterie plate at Bad Martha Farmer’s Brewery. This fun spot offers lawn games and live music on weekends.

Photo courtesy of Bad Martha Farmer’s Brewery


Day 3


Travel “up-island” (west) to Aquinnah for a breakfast of homemade codfish cakes and eggs at the Aquinnah Shop at the Gay Head Cliffs. Enjoy the expansive sea views of Vineyard Sound before heading down to popular Aquinnah Public Beach at the foot of the cliffs.


Swim and relax on this sandy stretch beneath the caramel and biscuit-coloured layers of rock. Then head to Chilmark’s fishing village in nearby Menemsha for a late lunch of local bluefish pâté at Larsen’s Fish Market.


Chilmark is the island’s last “dry town,” which means no alcohol is sold, though it can be consumed. Bring your own bottle to the Chilmark Tavern, where bartenders will uncork your wine or mix cocktails with whatever spirits you provide. For a taste of the island, eat pasta made from island-grown rye grain, paired with local heirloom tomatoes.

The Gay Head Cliffs, photo by Cindy Hopkins/Alamy


[This story appears in the July 2018 issue of WestJet Magazine]