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Beyond Boston: a Martha’s Vineyard guide

Fancy spending your summer holidays in New England? A tiny island off Cape Cod, Martha’s Vineyard is big on personality, with beautiful natural scenery and seaside attractions. Surrounded by the cool waters of the Atlantic, and with more than a third of its total land mass preserved from development, the Vineyard offers unparalleled water sports, scenic views and five historic lighthouses. And because the Vineyard doesn’t allow chains, there are plenty of locally owned shops, galleries and eateries to enjoy. Take a look at our Martha’s Vineyard guide for the best things to do on the island.

There are three main areas on Martha’s Vineyard – Edgartown, Oak Bluffs and Vineyard Haven, each with their own personality. With early 19th century Greek revival houses, Edgartown is more of a seaside village, while Oak Bluffs offers a beach-y vibe. Vineyard Haven has a little of both.

Getting There

Most visitors take the ferry service connecting the Vineyard and the mainland. If you’re driving from Boston it’s around a 90-minute trip to Woods Hole, Massachusetts, from where the state-run Steamship Authority ferries are the only option to accommodate cars, making multiple trips a day to Martha’s Vineyard. If you choose to bring your car aboard, a reservation will be needed to secure a spot but walk-ons are always welcome. Ferries dock in Vineyard Haven year round, and in Oak Bluffs mid-May through mid-October. There is also a seasonal passenger ferry service, including Island Queen from Falmouth, Hy-line Cruises from Hyannis, and Martha’s Vineyard Fast Ferry from North Kingston, Rhode Island.


Vineyard Haven

Stay: The Mansion House Inn is ideal for couples or families. It’s the only Island inn to offer an indoor pool and modern fitness centre with regular classes, and is located just two blocks from the year-round ferry terminal. In the heart of the newly established Vineyard Haven Harbor Cultural District, you’re in the middle of it all. For a distinctive inn experience with lovely water views and smashing breakfasts, check into The Crocker House Inn.

Eat: For dinner, it’s the Copper Wok, a newly opened hotspot that is already touted as a favourite among Islanders and visitors alike. You’ll delight in their saki-based cocktails and Asian-fusion. And no Vineyard trip is complete without a traditional visit to The Black Dog Tavern, a famous low-key family-friendly pub. For breakfast, try Art Cliff Diner or Nat’s Nook, the Island’s only creperie.

To Do: Explore the Vineyard Haven Harbor Cultural District for shopping and gallery hopping. Stop at Bunch of Grapes Bookstore for fact or fiction, and then visit Nat’s Nook’s some coffee and quiet reading time. Once you’re done, head up to the cupola of Mansion House for an incredible unobstructed view of the harbour. Get ready for the trek to the West Chop Lighthouse.


Oak Bluffs

Stay: A charming small inn that overlooks the ocean, Isabelle’s Beach House has a huge front porch that you’ll never want to leave.

Eat: When on the Vineyard, do as the locals do and grab a giant cup of chowder at the famous Martha’s Vineyard Chowder Company. For the ultimate one-stop shopping/dining/drinking, check out Beetlebung, the island’s first cocktail-focused lounge. Designed for the multi-tasker, it’s also a retail shop, daytime coffee house and nighttime dinner place with small plates full of ingredients native to the Island.

To Do: Take a slow stroll through Ocean Park for beautiful island views. Explore the maze of delightful gingerbread cottages and the Flying Horses carousel. Hit one of the amazing restaurants on the harbour or along Kennebec, including Red Cat for craft beer and whiskey, or Islander favourite, Offshore Ale.



Stay: Harbor View Hotel offers views overlooking the Edgartown Harbor and Lighthouse, with a great swimming pool and poolside bar. The Clarion Martha’s Vineyard is situated halfway between the beach and the town centre, so you have your pick of either location.

Eat: Not up for formal dining? Head to Henry’s Bar at the Harbor View Hotel for true farm-to-fork (or should we say, ocean-to-fork), menus. Alternatively, check out The Newes from America Pub (an Islander favourite and one of the best pubs on the island), upscale restaurant Alchemy, or waterside dining at Atlantic.

To Do: For the beach lovers, South Beach offers soft sand, big waves, seals, bird watching and private dunes. Take the Chappy Ferry over to Chappaquiddick and cycle to Mytoi Japanese Garden, or for a truly unique Vineyard experience take a Cape Poge tour and visit the Wasque Reservation. To preserve your memories, take pictures from the perch on Dock Street, right next to the Chappy ferry depot.

Pro Tip: Seafood lovers should make time to visit Menemsha during their trip to the island for fresh-off-the-boat lobster, oysters and steamers.


Written by Cheryl Fenton

Image credits:

Vineyard Haven Harbor © Martha's Vineyard Chamber of Commerce

Gingerbread Cottages © Martha's Vineyard Chamber of Commerce

Cape Poge Lighthouse © Martha's Vineyard Chamber of Commerce