Martha’s Vineyard: Down-Island

Slurp oysters, soar through the skies, and revel in the hustle and bustle of the social side of the island.

Getting the lay of the land aboard a Classic Aviators biplane. / Photograph by Christopher Churchill

Great Pond Beach

It’s generally accepted that the only way to avoid the throngs on the Vineyard’s few public beaches is to get your hands on a town beach permit. But finagling a private pass isn’t necessary to luxuriate in the lengthy expanse of Great Pond Beach, a sandy spit that separates Edgartown’s largest pond from the invigorating surf of the Atlantic. That is, if you can get there—the isthmus is accessible only by canoe or kayak, making it a haven for adventurers seeking a blessedly quiet retreat. Set out from the town launch at Meshacket Neck, then paddle a mile across the pond to the beach (note the wildlife and welcome lack of other humans along the way).

Or Try: Can’t fit all of your beach gear onto a paddleboat? Set up for the day at South Beach (also known as Katama Beach), where parking is plentiful and there’s lots of room to spread out on the soft sand.

The patio at Edgartown’s Port Hunter. / Photograph by Christopher Churchill

The Port Hunter

Plump and deeply briny with a hint of sweetness, the oysters farmed along Katama Bay are the food of summer on the Vineyard. And they’re best enjoyed by the dozen on the patio of Edgartown’s the Port Hunter—provided you can snag a coveted spot. When the sun goes down, the bustling, exposed-brick interior is the ideal place to kick back with a basil julep and, yes, more seafood: From Chatham mussels with red and green curry to fish tacos made with Vineyard flounder, the Port Hunter draws on all the fish in the sea for its creative menu.

Or Try: Getting cozy on the candlelit garden patio of the Sweet Life, a date-night staple since the ’90s.

Classic Aviators Biplane Tours

The hum of the engine. The wind whipping in your hair. The glorious views of Chappaquiddick, Aquinnah, and the sandy shores in between. You haven’t really seen the island until you’ve hopped aboard a bright-red biplane for a bird’s-eye view. Taking off from Edgartown’s Katama Airfield, Classic Aviators’ delightfully old-school tours give the lay of the land from open-cockpit planes. Flights range from 15 to 60 minutes and come with radio headsets so you can pipe up with questions—“Wait, is that Obama practicing his swing?”

Or Try: Ascend the spiral staircase of Chappy’s 217-year-old Cape Poge Lighthouse for a different kind of aerial view: The Trustees of Reservations offers tours.

A Classic Aviators biplane. / Photograph by Christopher Churchill

Winnetu Oceanside Resort

More than a century ago, the Mattakeset Lodge offered Edgartown visitors a true island escape: classic clambakes, dances under the stars, and, of course, gentle ocean breezes. Inspired by the retreat’s legacy, the Winnetu’s owners have taken a page from the same playbook, encouraging guests to slow down and savor the Vineyard’s simpler pleasures. Families still relish weekly clambakes, hosted just around the corner from a brand-new swimming pool and hot tub. They still leisurely meander along a path to the beach for good old-fashioned sun-soaking. And they certainly still gaze up at constellations from the property’s sprawling courtyards.

Or Try: The Arts and Crafts–style Nobnocket Boutique Inn, which recently received a bright, bold renovation. The boutique inn offers seven ultra-luxe rooms complete with Frette linens—and, naturally, croquet on the lawn outside.

A plate of Katama Bay oysters. / Photograph by Christopher Churchill


Jewelry designer Sioux Eagle knows a little something about island style, having spent the past 35 years helping tourists and locals alike accessorize their summer wardrobes at her eponymous Vineyard Haven shop. But away from the high-season crowds, she’s also well versed in the art of having a good time. Here, she shares her favorite down-island pastimes.

1. “The Featherstone Center for the Arts in Oak Bluffs has rotating art shows and wonderful outdoor concerts. It’s fun watching the kids run free while everybody else has their beach chairs, some wine, and an appetizer, listening to the music.”

2. “I love bowling, and the Barn Bowl & Bistro is just great family fun. They also have excellent food, so even if you’re waiting for lanes you can get something to eat.”

3. “The Vineyard Playhouse, in Vineyard Haven, always has something worth attending. It’s a real gem to be able to go to the theater and see such high-quality shows.”

Photograph by Madeline Bilis

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