Martha's Vineyard, Massachusetts: An Insider's Guide to a Perfect Summer Weekend

I've been spending summers on Martha’s Vineyard for years, and after countless weekends showing friends around the island, this is the version of the Vineyard I always recommend for a first visit. Rent a car when you arrive—you’ll want the flexibility, especially if you plan to explore up-island properly. What makes Martha’s Vineyard so special is how much range it packs into one relatively small island: six distinct towns, each with its own personality, from polished Edgartown and lively Oak Bluffs to the windswept, slower-paced western side of the island. In the summer, it’s also surprisingly easy to get to, with quick flights from New York and ferry service from Cape Cod, Nantucket, Rhode Island, New York, and mainland Massachusetts.

Friday: Down-island

Most people rush through Vineyard Haven, but it’s one of my favorite towns on the island—quieter, more local, and full of charm if you slow down enough to wander. Walk the harbor, pop into a few shops and galleries on Main Street, and down by the harbor, admire Gannon & Benjamin, the legendary wooden boatyard that feels like a living piece of old Vineyard maritime culture. For lunch, you really can’t go wrong with iconic The Black Dog Tavern, but if you want something more casual, grab lobster rolls or fresh sushi from The Net Result and eat outside on their picnic tables.

From there, head to Oak Bluffs for the afternoon. The Campground is worth seeing in person—rows of elaborately painted gingerbread cottages that somehow still feel whimsical instead of touristy, spilling out onto Ocean Park, a grand sweep of green with a bandstand gazebo overlooking the sound that feels straight out of a movie set.

State Beach is nearby and one of the easiest beaches on the island for a quick swim: calm water, easy parking, and usually a great breeze. You’ll also pass 'Jaws Bridge', where teenagers jump into the water below (the water has a bit of current, so do use caution if you want to partake).

Back in Oak Bluffs, for a casual dinner consider Offshore Ale or Lookout Tavern. Offshore feels more local and laid-back, while Lookout Tavern is ideal for drinks outside overlooking the water at sunset. After dinner, The Flying Horses Carousel is worth a stop as well—the oldest operating carousel in the country, spinning since 1876 with hand-carved horses and real horsehair manes, and immortalized by the indie roots-rock band Dispatch with the line "stole the ring from the Flying Horses." For a late-night treat, head to back door donuts or ice-cream at Mad Marthas.

On Saturday, I recommend “heading 'up-island,” which feels like an entirely different place. Start at the West Tisbury Farmers Market, one of the best summer markets anywhere in New England. You’ll find flowers, produce, pastries, and locally-made goods, but don’t miss Rusty’s Tomatoes or Salt Rock Chocolate. Keep your eyes open; the market has a well-earned reputation for celebrity sightings, with notable island regulars known to turn up among the stalls.

Alley's General Store is just down the road and worth popping into, and across the street, the Field Gallery sculpture garden is one of those quietly beautiful Vineyard spots people remember long after the trip.

From there, take Middle Road toward Chilmark—one of the prettiest drives on the island, especially in the summer when everything is green and overgrown. Stone walls, horse farms, open fields, old trees arching over the road—it’s classic 'up-island' Vineyard.

Tucked into the island's northwest corner, Menemsha is Martha's Vineyard's most authentic fishing village—a tiny working harbor where lobster boats and swordfish harpooners still go out at dawn, the docks smell of brine and rope, and the whole place feels blissfully immune to polish. For lunch, The Homeport is the sit-down option, where you order at the counter and wait for your buzzer on the deck; Larsen's Fish Market is a grab-and-go alternative, with seating available on lobster pots outside—regulars know to bring a beach chair for busy days. Either way, finish with soft serve from The Galley, a longtime family-run spot whose deck is lined with photos from the filming of Jaws.

Continue your drive farther up-island to Aquinnah, the Vineyard’s westernmost town, where the landscape becomes noticeably wilder and more dramatic. The Aquinnah Cliffs are every bit as striking in person as they are on postcards—layered clay cliffs dropping into the ocean, with some of the best views anywhere on the East Coast. The cliffs sit on Wampanoag land and have enormous cultural significance in addition to being incredibly beautiful. If you don’t mind a short walk, head down to the beach below. One thing to note: the beach becomes a nude beach further along—entirely normal by local standards, but worth knowing in advance.

Still in Aquinnah, the former Kennedy property is worth a visit—300 acres of oceanfront dunes, wooded trails, kettlehole ponds, and open meadows that were once part of Jackie Kennedy's beloved Vineyard retreat, purchased in 1979 and where the family spent summers for decades. The land was recently sold to the Sheriff's Meadow Foundation and the Land Bank and is now open to the public. Walking it gives you a genuine glimpse into the kind of private, remote beaches that people—and piping plovers—return to the Vineyard for year after year: pristine, windswept, and magnificent in a way that's hard to find on the East Coast. Just make sure to reserve parking ahead of time.

On the return, stop at Chilmark General Store or Beetlebung Farm if the mood strikes for a snack or locally-sourced goods before rejoining South Road for the cruise back down-island.

Back in Edgartown, there’s no shortage of great dinner options depending on the kind of evening you want. Alchemy is lively and energetic with great cocktails and a buzzy dining room that always feels fun in the summer, while L’étoile is more intimate and refined—perfect for a slower, more polished dinner tucked inside a beautifully restored captain’s house. If you’re willing to wait a bit for a table, Port Hunter is always a scene in the best way: dimly lit, loud, crowded, and one of the few places on the island that genuinely feels like nightlife.

Save the last day for Edgartown, most of which is easily explored by bike. For brunch, Katama Kitchen is a relaxed, family-owned spot set on the Katama Airfield, with outdoor picnic tables and the occasional biplane taxiing past; Morning Glory Farm is a working family farm that has been feeding the island for generations, where the baked goods are made from scratch and the produce was growing in the field behind you yesterday. Either way, eat outside at the picnic tables and take your time.

If you're craving some beach time, nearby South Beach is one of the best public beaches on the island—three miles of open Atlantic shoreline with rolling surf, soft dunes, and enough space to spread out even in peak summer. The waves are noticeably rougher here than State Beach, which is part of the appeal, especially for boogie boarding, long walks, or just spending a few hours on a classic Vineyard surf beach.

Spend the rest of the day wandering Edgartown itself. Walk out to the lighthouse, browse the shops along Main and North Water Streets, and keep an eye out for the 3-car On Time ferries crossing back and forth to Chappaquiddick. For drinks, settle onto the porch at Harbor View Hotel or the deck at Faraway. Harbor View, especially, is one of those classic Vineyard spots that fully lives up to the hype on a summer afternoon.

Then just wander. Edgartown is at its best when you don’t over-plan it—white clapboard houses, hydrangeas everywhere, sailboats in the harbor, and streets that somehow still feel elegant without trying too hard. Conclude the weekend with an early dinner at The Atlantic overlooking the Edgartown harbor and Yacht Club before heading home.