Beyond Boston: A Martha’s Vineyard Guide

By: Cheryl Fenton

July 15, 2014

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 fun to enjoy. Surrounded by the waters of the Atlantic, and with more than one-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 major areas on Martha’s Vineyard “”Edgartown, Oak Bluffs and Vineyard Haven””each with its 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.

 harbor aerial view | Martha's Vineyard Guide

Aerial view of the pretty habour © Martha’s Vineyard Chamber of Commerce

Getting There

Ferry arrives in vineyard haven | Martha's Vineyard Guide

Ferries arriving from the mainland © Martha’s Vineyard Chamber of Commerce

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 more than 20 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.

The Black Dog Tavern | Martha's Vineyard Guide

The Black Dog Tavern is a firm favourite among vacationers © Martha’s Vineyard Chamber of Commerce

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 the newly opened 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.

Beetlebung | Martha's Vineyard Guide

Inside Beetlebung, the island’s new cocktail lounge © Melissa Ostrow

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 new Beetlebung, the island’s first cocktail-focused lounge. Designed for the multitasker, it’s also a retail shop, daytime coffee house and nighttime dinner place with small plates full of ingredients native to the Island.

Gingerbread cottages | Martha's Vineyard Guide

Gingerbread cottages line the streets around Ocean Park © Martha’s Vineyard Chamber of Commerce

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, the brand new craft beer and whiskey bar, or an Islander favourite Offshore Ale.

Inside Offshore Ale | Martha's Vineyard Guide

Sample some craft beers at Offshore Ale © Martha’s Vineyard Chamber of Commerce


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 located halfway between the beach and the town centre, so you have your choice of it all.

Local seafood dishes on offer | Martha's Vineyard Guide

From ocean to fork, enjoy the island’s great tasting seafood © Martha’s Vineyard Chamber of Commerce

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

Mytoi gardens | Martha's Vineyard Guide

Lap up the verdant surrounds at Mytoi Japanese Gardens © Martha’s Vineyard Chamber of Commerce

To Do: For the beach lovers, South Beach offers super soft sand, big waves, seals, bird watching and private dunes. Take the Chappy Ferry over to Chappaquiddick and cycle to Mytoi Japanese Garden. 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. Walk up North Water Street and visit Edgartown Harbor Light for shots of Old Whaling Church.

A proud feather in Massachusetts’ cap, Martha’s Vineyard is a gorgeous world ready to explore.

Header image: Edgar Habour lighthouse © John Kropewnicki/iStock/Thinkstock

Virgin Atlantic operates daily flights to Boston from London Heathrow. Book your flight today.

Have you been to Martha’s Vineyard? Have we left anything out of our Martha’s Vineyard guide? Let us know in the comments section below.

Written by Cheryl Fenton


Cheryl Fenton

A Boston native, Cheryl Fenton is no stranger to the goings on and hot spots of her favorite city. Throughout her 15-year freelance career in dining, fashion, beauty and travel, Cheryl has covered it all for local magazines and websites including Stuff, The Boston Globe, Boston Phoenix, and Boston Common. You can also find her national bylines in glossies such as Glamour, Cooking Light, and Wallpaper. In her spare time, what little there is, Cheryl strolls the city with coffee in hand, always looking for what’s next on the agenda.

Categories: Our Places