Insider’s Guide to Martha’s Vineyard | Eat, Stay & Play

Planning a Martha’s Vineyard vacation? Writer and resident Jamie Kageleiry shares her expert picks for the best places to eat, stay, shop, and things to do for the ultimate insider experience.

By Jamie Kageleiry

Feb 25 2022


Make Your Own Perfect Vineyard Day

Photo Credit : Elizabeth Cecil

TRAVEL NOTE: Since many businesses and venues are adjusting their operations in response to COVID-19 health concerns, please contact them directly or check their websites before making travel plans.

In the March/April 2021 feature “A Beautiful Hiding Place,” writer and resident Jamie Kageleiry shared an insider’s perspective on the many ways to find refuge on the fabled Massachusetts island of Martha’s Vineyard. Planning your own Vineyard vacation? Don’t miss Jamie’s expert tips on the best places to eat, stay, shop, and play for your own insider experience.

Dozens of miles of trails and endless destinations await on Martha’s Vineyard
Photo Credit : Elizabeth Cecil

Insider’s Guide to Martha’s Vineyard | Eat, Stay & Play

Martha’s Vineyard Restaurants

Alchemy | Edgartown
One of this author’s personal favorites for going on 25 years now. Eat on the terrace or the porch overlooking Main Street. 

The Black Dog Tavern | Vineyard Haven
The place to go for terrific tavern food, right on the beach.

Dock Street Coffee Shop | Edgartown
Classic diner burgers at a counter, or takeout, on the harbor.

Lucky Hank’s | Edgartown
Comfort-food specialist offering picnic tables under twinkly lights.

Mocha Mott’s | Oak Bluffs and Vineyard Haven
The Vineyard’s coolest coffee hangout.

Noman’s | Oak Bluffs
Most of the seating here is outdoors, with fire pits, music, and games like cornhole. Great menu with solid options for family dining. 

Orange Peel Bakery | Aquinnah
Everyone knows Julianne Vanderhoop, whose family has run restaurants in Aquinnah for generations. Don’t miss bring-your-own-topping pizza nights. Aquinnah; 

The Pawnee House | Oak Bluffs
New in 2020, and featuring plenty of yummy vegan dishes to choose from. 

Salvatore’s | Vineyard Haven
Another newcomer in 2020, serving top-notch Italian fare right off Main Street.

State Road | West Tisbury
An up-island eatery popular with in-the-know Vineyarders. 

The Sweet Life | Oak Bluffs
A favorite of the Obamas, offering takeout or terrace dining.

Favorite Martha's Vineyard Hotels
The Outermost Inn in Aquinnah
Photo Credit : Chris Laursen

Martha’s Vineyard Hotels & Inns

Harbor View Hotel | Edgartown
Classic New England grand hotel overlooking the harbor; cocktails on the porch can’t be beat.

Lambert’s Cove Inn | West Tisbury
Farm-fresh meals and access to Lambert’s Cove Beach, one of the island’s most beautiful beaches.

The Oak Bluffs Inn | Oak Bluffs
Classic in-town Victorian charmer with rooftop cupola. 

Outermost Inn | Aquinnah
Sunsets, wildlife, and great food and lodging in an enchanting Aquinnah location. 

Shearer Cottage | Oak Bluffs
Five cozy studios with wraparound porches, nestled in the Highlands of East Chop.

Winnetu Oceanside Resort| Edgartown
Cottages, pools, Atlantic beach, and at the Dunes restaurant, one of the best meals you’ll have all summer.

Martha’s Vineyard Shopping

Art Galleries
Martha’s Vineyard is dotted with some 40 galleries, from Groovy Sue and Cousen Rose in the Oak Bluffs Arts District to West Tisbury’s Granary Gallery, the oldest and largest art gallery on the island. Check out the directory at Martha’s Vineyard Online:

Bunch of Grapes Bookstore | Vineyard Haven
Extensive collection of island authors—William Styron, Lillian Hellman, John Hersey, Jules Feiffer, etc.—including some signed copies. 

Edgartown Books | Edgartown
A Main Street mainstay with a great café in back. 

Featherstone Center for the Arts | Oak Bluffs
Celebrating its 25th year in 2021, the island place for gallery shows, arts programs, and community events also boasts a summertime flea and fine arts market. 

Stina Sayre | Vineyard Haven
Women’s European-style clothing from a Swedish-born champion windsurfer turned designer.

Vineyard Artisans Festivals | West Tisbury
Regular showcases of island-made clothing, jewelry, dishes, and more, from May to December.

West Tisbury Farmers’ Market | West Tisbury
Local produce, cheeses, meats, shellfish, condiments, and more, offered twice weekly from mid-June through October. 

Martha’s Vineyard Things to Do

African-American Heritage Trail of Martha’s Vineyard
Highlighting more than 30 sites, including the Shearer cottage and the homes of Adam Clayton Powell Jr. and Dorothy West.

Aquinnah Cultural Center | Aquinnah
Housed in a historical Wampanoag family homestead and filled with exhibits describing the lifeways of the island’s earliest residents.

Bike Trails
Dozens of miles of trails and endless destinations await (including, after a short ferry hop to Chappaquiddick, the lovely Japanese garden Mytoi). 

Felix Neck Wildlife Sanctuary | Edgartown
Featuring miles of trails through beautiful woodlands, meadows, and salt marshes, and out to the shores of Sengekontacket Pond. 

Greetings from Martha’s Vineyard Tours
Locals with the inside scoop lead these driving tours, which culminate in a seafood picnic by the water.

Island Spirit Kayak | Oak Bluffs
Proprietor Chick Stapleton dispenses kayaks and paddleboards from astand at Little Bridge; tours and beach party events too. 

Martha’s Vineyard Museum | Vineyard Haven
Learn about everything from suffragism on the Island and whaling history to Thomas Hart Benton and Jaws. Don’t miss the bookshop and the one-of-a-kind collection of oral histories from the museum’s own Linsey Lee. 

Walking Trails
The Land Bank trail around Farm Pond in Oak Bluffs, West Chop Woods in Vineyard Haven, Sepiessa Point Reservation in West Tisbury, Sheriff’s Meadow Sanctuary in Edgartown—explore all these and more with links to the properties and a trail app.

Wind’s Up | Vineyard Haven
Water sports sales and rentals of all kinds—surfboards, sailboats, and more—plus gear and lessons.