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 CecilAlchemy | 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 HavenThe 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 HavenThe 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 HavenAnother 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.
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.
Art GalleriesMartha’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 | EdgartownA 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 TisburyLocal produce, cheeses, meats, shellfish, condiments, and more, offered twice weekly from mid-June through October.
African-American Heritage Trail of Martha’s VineyardHighlighting 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 TrailsDozens 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 ToursLocals with the inside scoop lead these driving tours, which culminate in a seafood picnic by the water.
Island Spirit Kayak | Oak BluffsProprietor Chick Stapleton dispenses kayaks and paddleboards from astand at Little Bridge; tours and beach party events too.
Martha’s Vineyard Museum | Vineyard HavenLearn 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 TrailsThe 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 HavenWater sports sales and rentals of all kinds—surfboards, sailboats, and more—plus gear and lessons.