Martha's Vineyard: Where the Country Meets the Sea

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Advisor - Domonique Matthews
Curated By

Domonique Matthews

  • Active Travel

  • Arts & Culture

  • Beaches

  • Family Travel

  • Massachusetts

  • Coastal

  • Local Culture

  • Local Food

A boat at sea as the waves gently lap the shore on a sunny day.
Curator’s statement

As a West Coaster, Martha's Vineyard always sounded something like a fantasy. Where one would hob knob with the likes of presidential families vacationing in large compounds most of us would never experience. What we discovered was a bucolic island of country roads, quiet beaches and roadside farm stands. A place where people are neighborly and courteous, and the pace of life is slow and easy.

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Where to stay in Massachusetts

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Things to do in Massachusetts

A cheerful restaurant shiplap exterior surrounded by shrubs and foliage on a sunny day.
  • Beaches - So many beautiful beaches and coves to discover on the island. From the long stretches of South Beach and State Beach to a smaller section of up-island coast like Lucy Vincent Beach there's a spot for everyone. Menemsha Beach is perfect for sunset and, for those who like to surf, Squib Nocket Beach is a popular go-to.

  • Shopping - I can't get enough of the boutiques and vintage shops around the island. Try Sea Legs or Slate in Edgartown for women's clothing and Second Treasures for vintage finds.

  • Artist Studios - Martha's Vineyard is known as an artist haven. I love how many have open studios for shoppers to browse while they are working. A favorite is Chilmark Pottery.

  • Farm Stands - You can't go far in Martha's Vineyard without stumbling across a farm stand, especially up-island. We love to pop into Bettlebung and The Grey Barn & Farm in Chilmark.

  • Family Fun - Oak Bluffs is a fun little town reminiscent of the early 1900s with the oldest operating platform carousel in the United States. Try your luck at grabbing the Golden Ring!

  • For the Adventurer - You can parasail, take surf lessons, rent SUPs, find a fishing guide or charter a boat. Definitely take it to the ocean.

  • Farmer's Market - We sure love the Farmer's Market in West Tisbury. Here you can enjoy hot coffee, freshly baked cinnamon rolls and breakfast burritos all while strolling about picking out veggies for dinner.

Places to eat & drink in Massachusetts

Wind whips through the reeds that line the shore as boats float toward the horizon on a cloudy day.

So much incredible farm to table food on island from farm stands to cafes to high end restaurants; you can't go wrong. Here are a few favorites:

  • 7A Foods - A great place to start your day with fresh hot coffee, bagels and pastries.

  • Chilmark General Store - Stock up on your beach picnic essentials or order yourself a pizza or sandwich to eat on the big wooden porch.

  • Little House Cafe + Bakery - Perfect casual spot down-island. Try the BLT!

  • Homeport - The best lobster rolls on the island and a beautiful casual setting on the Menemsha Creek.

  • State Road - Perfect little tavern done farm-style with its own lovely farm garden.

  • Beach Road - Beautiful contemporary restaurant with views over the lagoon.

  • The Grey Barn - A small New England Farm with creamery, bakery and farm stand.

  • Chilmark Tavern - Farm to table classics and island fresh produce. As with a lot of Martha's Vineyard, it's BYOB. The Tavern will mix cocktails for you with your BYOB using their mixers and mocktails.

Advisor - Domonique Matthews

Travel Advisor

Domonique Matthews

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This guide is a part of our ongoing series on travel to Massachusetts. For more travel tips, check out Fora Advisor Tammy Kiefer's guide, Martha's Vineyard: The Perfect Fall Getaway.