24 Hours in Martha's Vineyard

The movie that put Martha’s Vineyard on the map warned “Don’t go in the water,” but this popular Massachusetts isle has outgrown Jaws’ legacy to become a go-to getaway for swimmers, surfers and seafood lovers.

Although just 100-square-miles, the island now caters to an even broader spectrum of vacationers. They flock here in-season (from April onwards) for the perfect blend of laidback vibes and island favorites – from cozy beer taverns to seafood shacks and hidden beaches. Of course, all of this can be avoided; the island has plenty of nooks and crannies for in-betweeners.

Stay at Menemsha’s Beach Plum Inn and experience what it was like for the island’s fishermen 350 years ago, rising early for a day at sea. The only difference is, they probably didn’t rest anywhere quite as comfortable as the cottages where you’ll be staying, complete with antique bed frames, harbor views and an on-site chicken coup.

50 Beach Plum Lane, Chilmark

There was a time when small towns like the ones on Martha’s Vineyard had one store and one store only. The General Store, like this one in Chilmark, provided everything you could possibly need and more. Don’t just stock up on supplies here though – sit down for a breakfast of bagels with smoked salmon or cage-free eggs, then head outside. The food tastes best from the porch.

7 State Road, Chilmark

Take a 30-minute drive to Edgartown for one of the best beaches on the island. South Beach’s strong surf and three miles of sand are a must-do, no matter how short your stay. Stick around long enough and you might meet the local seals.

South Beach, Edgartown

When you get to Oak Bluffs – a 15-minute drive from Edgartown – you’ll quickly notice the rows of tiny colorful “gingerbread houses.” Once a campground for Methodist church retreats, the surrounding area sprouted hundreds of tiny Carpenter Gothic-style cottages in the mid 1800s. Some of these homes have been passed down through generations, while others are rented out to vacationers. No matter who’s inside, these miniature, multicolored homes make for an Instagram-worthy National Historic Landmark.   

Wesleyan Grove, Oak Bluffs

The Vineyard and Nantucket Sound once saw more ships than any other place in the world besides the English Channel. Get the lay of the land by visiting one of the island’s five famed lighthouses. The East Chop Lighthouse in Oak Bluffs is of particular interest to historians because it stands on the site of one of the first telegraph signals, set up in 1828. For non-history buffs, the view from the top is easily one of the island’s best.

229 East Chop Avenue, Oak Bluffs

Named after a popular island pup, the famous Black Dog Tavern was the island’s only year-round restaurant when it opened in 1971. It’s still the perfect place to get your fix of chowder and freshly caught cod, while the roaring trade done by its gift shop is a testament to its reputation. On Martha’s Vineyard, visitors and locals wear the Black Dog with pride.

20 Beach Street Extension, Vineyard Haven

Post-dinner hours are quiet on the island. But before you succumb to sleep after your action-filled day, pack in an hour or two of dancing to live music among locals at The Ritz (don’t let the name put you off – it’s a lot more laid-back than it sounds).

4 Circuit Avenue, Oak Bluffs

While late nights might be hard to come by on Martha’s Vineyard, there’s always something going on at the Martha’s Vineyard Gourmet Cafe and Bakery. Despite being an unusual night spot, from 7 p.m. to 1 a.m. the back of this beloved bakery turns into a donut shop renowned for freshly baked dollar donuts and apple fritters ($3.50). Before 7 p.m., the bakery is also a great spot for coffee and a sweet snack.

5 Post Office Square, Oak Bluffs

With six towns to explore (and plenty of natural beauty), it’s possible to pack a smallish bag and manage Martha’s Vineyard in a weekend. The island is only accessible by private boat, ferry (which you can take your car on if you’d like) or plane to Martha’s Vineyard Airport, but once you’re there getting around by car, public bus, or bicycle is a cinch. Just be sure to hit these must-see spots.

Take it from someone who grew up in Martha’s Vineyard: our MarkMaker and chef Chris Fischer discusses life on the island and how it inspires his work.