Things to do in a week on Martha’s Vineyard

If you’re lucky enough to spend a full week on Martha’s Vineyard rather than passing through as a day-tripper, savor every minute of it. The island rewards the unhurried visitor — six distinct towns, each with its own personality, its own beaches, and its own reasons to linger. Here’s how I’d spend a week, from someone who knows and loves every corner of it.

Oak Bluffs

Oak Bluffs is the liveliest town on the island — full of shops, restaurants, ice cream, and the wonderful energy of a New England summer in full swing. Walk Circuit Avenue, get ice cream, wander into the shops, and watch the world go by from Ocean Park.

Don’t miss the historic Flying Horses Carousel — the oldest operating platform carousel in America. Watch the riders try to grab the brass ring as they spin past. It’s one of those charmingly old-fashioned summer moments that’s hard to find anywhere else.

And of course — wander through the gingerbread cottage neighborhood in the Campground. Over 300 Victorian carpenter gothic cottages painted in candy colors, lining narrow lanes that feel like something out of a fairytale. Go in the early morning or late afternoon for the best light and fewest crowds. It’s free, it’s unforgettable, and it’s unlike anything else in New England. And if you love them so much you want to stay in one — we list several of these extraordinary cottages on our site.

Vineyard Haven

Your first stop on the island should be Vineyard Haven — it’s where the ferry docks, and it’s worth more than a quick pass-through. The town has a lovely main street with galleries, boutiques, and shops worth browsing. And of course — the Black Dog Tavern.

The Black Dog Tavern opened on New Year's Day 1971, born from Captain Robert Douglas’s frustration at finding no year-round restaurant on the island — a dream sketched out on a napkin that became one of the most beloved institutions in New England. It sits right on Vineyard Haven Harbor, and the views from the patio on a sunny day are as good as the food. Get the chowder — it’s been famous since day one.

Before you leave, stop into the Black Dog General Store next door and pick up the classic souvenir: a Black Dog hoodie or t-shirt. The iconic logo is recognized worldwide, and wearing one is a quiet signal that you've been to the Vineyard. It's a rite of passage.

And while you’re in Vineyard Haven — don’t miss Island Alpaca. You can feed the alpacas, browse their charming shop full of alpaca wool items, and generally have a delightful time. I’ve been, and it’s every bit as wonderful as it sounds — especially if you have kids in tow.

Edgartown

Drive the white picket-fenced streets of Edgartown and you’ll understand immediately why people fall in love with this town. It’s stately, beautiful, and immaculately kept. Stop by Morning Glory Farm for fresh flowers, produce, and baked goods — their salad bar is wonderful for a casual lunch.

Make your way to Edgartown Lighthouse, set against beach grass, white sand, rosa rugosa, and the lovely harbor. It’s one of the prettiest spots on the island at any time of day.

And if you happen to be driving over the bridge between Edgartown and Oak Bluffs — keep an eye out for the “Jaws Bridge” on Beach Road. In summer, locals and visitors alike jump off it into the channel below. I’ve watched people do it with great enthusiasm. It’s become something of a summer tradition — and if you’re feeling brave, apparently it’s a rite of passage.

West Tisbury

West Tisbury has a quiet, agricultural charm that feels completely different from the busier parts of the island. Stop at the West Tisbury Farmer’s Market — held every Wednesday and Saturday — for fresh bread, local produce, flowers, and the chance to shop alongside actual islanders. Get there early for the good bread.

Lambert’s Cove Beach is one of the island’s most beautiful and most beloved beaches — tucked away off Lambert’s Cove Road, with a short 5-10 minute walk through a lovely wooded trail to the dunes and the water. Sunsets here are spectacular. Worth every step of the walk.

Chilmark

The drive out to Chilmark is an experience in itself. The road becomes increasingly pastoral the further you go — rolling hills, beautiful old farmhouses, horse farms, sheep grazing in open fields. It genuinely slows you down in the best possible way.

Lucy Vincent Beach is one of the most beautiful beaches on the island — remarkable rock formations, stunning scenery. Worth knowing before you make the drive though: it’s a restricted town beach, exclusive to Chilmark residents, their guests, and those renting property in Chilmark during the summer. If that’s you — wonderful, you're in for a treat!

Menemsha

Menemsha is my favorite village on the island. This tiny fishing village — used as a backdrop in the original Jaws, if you look closely — is the most authentically “New England” place I've ever been — and I was born, raised, and spent most of my life here. Weathered fishing shacks, lobster traps stacked on the docks, boats coming and going. It feels completely real in a way that’s increasingly rare.

Eat at the Menemsha Galley — order at the counter, settle into the dining room that feels like you’re sitting right in the harbor, and get the swordfish sandwich if it’s available that day. Or grab a lobster roll at Larsen’s Fish Market right on the dock — simple, fresh, and completely perfect.

And stay for sunset if you possibly can. Menemsha faces west, and the sunsets here over the water are extraordinary. Locals bring a bottle of something cold, find a spot on the rocks, and watch the sun drop into the Sound. Do the same. You’ll thank yourself.

Aquinnah

Drive all the way out to Aquinnah for the views of Gay Head — the dramatic clay cliffs tumbling down to the water, the lighthouse perched at the top, and on a clear day, views stretching all the way to the mainland. It’s one of those places that genuinely stops you in your tracks. Pull over, take it in, and stay longer than you planned.

While you’re here, Lobsterville Beach on the north side is a lovely, quieter alternative to the more well-known spots — beautiful and often far less crowded.

One More Thing Worth Knowing: Chappaquiddick

I haven’t done this yet myself, but it’s on my list — and a local told me it’s wonderful. A short ferry ride from Edgartown takes you to Chappaquiddick Island, where you’ll find Mytoi Garden, a Japanese-inspired garden that’s completely unexpected and completely lovely. If you have a free afternoon and want to feel like you’ve discovered something, this is apparently it.

Martha’s Vineyard is the kind of place that gets under your skin. One week is never quite enough — but’ a very good start.

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