Travel Guide: Avoid the Crowds With an October Trip To Martha’s Vineyard

Shoulder season on the island was practically made for socially distanced fall getaways. Here’s how to do it right.

A picture-perfect view of Lighthouse Beach in Edgartown. / Photo by Alison Shaw

It used to be that the Tuesday after Labor Day, you could almost hear a sigh escape from all corners of Martha’s Vineyard as the last of the summer crowds boarded their ferries home. With many seasonal homeowners extending their island stays because of the pandemic, this year has been a little different, but the relaxing pace of October on the Vineyard—warm days, cool nights, fewer people, and water still pleasant enough for taking a dip—is unchanging.

To soak it all up, head outdoors. No matter your home base, the TrailsMV app will steer you toward a hiking trail that fits your needs, from Mytoi, a Japanese garden on Chappaquiddick, to the rugged terrain of Menemsha Hills in Chilmark, where sweeping water views are your reward for summiting the peaks. At West Tisbury’s Polly Hill Arboretum, meanwhile, fall’s glory is on full display. Swimming more your speed? Make your way to any island beach, including Lucy Vincent in Chilmark and Lambert’s Cove in West Tisbury, where residents-only restrictions are lifted come fall. (Pro tip: Waters on the Vineyard’s south side will be warmer than on the north side, though with more waves.)

If your idea of a good island dinner starts in your own rental kitchen, there are plenty of options for staying well fed. The West Tisbury Farmers Market, which continues on Saturdays through October 10, offers the freshest of bivalves from Spearpoint Oysters, bread such as island-grown rye from Cinnamon Starship, and bonbons from Salt Rock Chocolate (they often sell out, so it’s a good idea to preorder). And for those who prefer to have the food come to them, popular island caterer V. Jaime Hamlin has pivoted to offering home delivery of three-course meals (think: local sea scallops atop corn succotash) on Thursdays, Fridays, and Saturdays.

Evenings out on the town, on the other hand, should always start with outdoor beers at Bad Martha Farmers Brewery in Edgartown. After a round or two, make your way to Nomans in Oak Bluffs for elevated comfort food (mojo pork tacos, yucca fries, and banh mi with smoked and fresh local fish) and live music out on the lawn. Then breathe in the crisp air and relax: Shoulder season has officially arrived.

Getting There

Three boats can get you across the sound: The Steamship Authority runs multiple ferries out of Woods Hole daily, with reservations needed for vehicles. Hy-Line Cruises runs ferries out of Hyannis through October 25, and the Island Queen runs out of Falmouth through October 12; both are passenger only.

Staying There

This year—and this time of year—are made for house rentals. “October is a great time to come to the island,” says Daniel Becker, a Cape Cod–based general manager at the vacation rental company Vacasa, which has a variety of properties available across the Vineyard, including homes with ocean access, pools, and fireplaces to cozy up to. “There’s still plenty to do and see, but it’s quiet enough so you can go around the island at your leisure.”