A Weekend on Island Time: The Insider’s Guide to Martha’s Vineyard
Martha’s Vineyard versus Nantucket is a rivalry as old as time. Both are tiny New England islands off the coast of Massachusetts (though the Vineyard is larger), and each has inspired a devout fan base (though the Vineyard boasts the Obamas). In case you can’t tell, we’re team Martha’s Vineyard for this edition of car-free weekend travel. (But don’t worry: We’ll cover Nantucket another day.) Take a ferry to Edgartown on a Friday afternoon, and stay for as long as you possibly can — after even a single afternoon, you won’t ever want to leave. Read on for the best spots to eat, drink, and explore on this historic island.
For a weekend visit, Edgartown is perfect, because it’s the bustling center of the island’s activity. We recommend booking a house over a hotel: Consult Airbnb, VRBO, or WeNeedaVacation for rentals. You’d be surprised at the quality of the cottages available, especially in the off-season.
If you’d rather stay somewhere that someone else is picking up after you, the Harbor View Hotel is a classic option, as are The Charlotte Inn and Hob Knob — though all three are expensive (and commensurately luxurious). The Ashley Inn is more affordable, without sacrificing that Vineyard charm, and offers a delicious breakfast every morning (and cookies and lemonade every afternoon).
When on Martha’s Vineyard, you’ll want to go to the beach (obviously). South Beach, out in Katama, is the main public beach on-island. Try to find someone with a car (and a season permit pass) to drive out over the sand to Norton Point. Make a pitstop at Katama General Store for everything you may have forgotten for the beach: boogie boards, ice, beer, sunscreen. If you want to relax and avoid the crowds, head up-island to the smaller beach in Menemsha. Visit the neighboring fishing wharves to grab a lobster roll at Larson’s Fish Market, where you can watch the lobsters being taken from the boats to the tanks (now that’s fresh).
For the most Insta-worthy opportunity on Martha’s Vineyard, head up to Aquinnah to explore the cliffs surrounding Lucy Vincent Beach. The drive is long, but it’s worth it to take a picture with your friend/S.O./frenemy with the lighthouse in the background (expect triple-digit likes). If you start to notice as you walk down the shore that people are becoming less clothed, don’t be alarmed: The end of the beach closest to the lighthouse is a nude beach, and sand is a great exfoliant.
If you’re looking for a more active getaway, this is also a spot with the best hiking trails on the island. For kayaking and paddleboarding, head to either Lagoon Pond in Vineyard Haven or Sengekontacket Pond — the water is calm and quiet. Go windsurfing or kiteboarding at Joseph Sylvia State Beach, which is also home to the famous Jaws bridge — maybe get a picture of yourself jumping off — or charter a boat to go fishing from Oak Bluffs. Be sure to stop by Nancy’s afterward for frozen rum drinks and a taste of the other side of Martha’s Vineyard.
Finally, a visit to the Island Alpaca Company is the perfect unexpected addition to your trip. The animals are adorable, the gift shop is full of incredibly soft items you never knew you needed (alpaca cape, anyone?), and it may rival the lighthouse as the most Insta-worthy moment of the trip. After all, who can resist a selfie with an alpaca?
To witness the best sunset on the island, grab dinner at The Beach Plum Inn in Menemsha: The romantic ambiance makes it a perfect date spot. The outdoor garden of Atria in Edgartown is another Instagram-worthy option for a date night, while the much more casual downstairs burger cellar is a great spot to grab a bite before a night out. L’Étoile is another fancy dinner option if you’re looking to splurge because #You’reWorthIt. But if you have to pick just one upscale restaurant, head to Alchemy: The pinnacle of fine dining in Edgartown, this restaurant is a classic that should be visited at least once.
Head up-island to State Road or Beach Road: These two sister restaurants boast seasonal farm-to-table menus that capitalize on the Vineyard’s agricultural scene. Other dinner options include Home Port in Menemsha and sushi at the Lookout Tavern in Oak Bluffs. For a local spot, The Newes from America Pub is dark with low ceilings and beer tokens for regulars (some patrons even have their own brass plaques on bar stools). It makes a good choice for when everywhere else is crowded or you want to linger around a table on an off-night.
For breakfast, check out Rosewater Market or Among the Flowers Café, where you’ll enjoy terrific omelets and cute outdoor seating (but beware the long line). The Black Dog Bakery Café is a tourist stop, but it’s worth it for a one-time trip to the island. The diner scene on Martha’s Vineyard is also not to be missed: Head to Artcliff Diner early in the morning to avoid an hours-long wait (it’s worth it), or check out the Right Fork Diner or the Dock Street Coffee Shop for the best greasy breakfast sandwich.
Hike up-island for lunch at one of the picnic tables at the Scottish Bakehouse in Tisbury for farm-fresh cuisine. You could also pick up sandwiches at Humphreys Bakery or hit up the salad bar at Morning Glory Farm before heading to the beach. Espresso Love also has a lot of outdoor seating and an amazing curry chicken salad for lunch.
If at some point you find you’ve managed to skip dinner altogether, head to Back Yard Taco, which is open until half past midnight. Back Door Donuts also sells donuts out of the back door of a bakery in Oak Bluffs at night — the line can get pretty long on Saturdays, but it’s well worth the wait.
The Atlantic is a must-visit on your trip to Martha’s Vineyard: The waterfront bar and restaurant in Edgartown often called “Hotlantic” by regular visitors. You can check out the live music playing in the front of the bar on summer weekends, though the back bar is often the best scene. Boasting a great outdoor space right on the water, it’s a bit expensive but always a good time.
The Port Hunter is the nightlife spot to avoid the riffraff at The Seafood Shanty in Edgartown — unless you’re interested in that kind of debauchery (but more on that later). Similar to the Atlantic, The Port Hunter also frequently host live bands, so be sure to book a dinner reservation to beat the crowds that show up later in the evening. When you do, order the local Katama honeysuckle oysters — they’re truly the best oysters on the planet (a subjective but definitive opinion you will surely share). Their sister restaurant/bar, The Covington, also has a good scene and is conveniently located right across the street.
Now, back to the Shanty: This bar is perfect for an afternoon drink in the sun or to watch a sports game on a rainy day (or football in the fall). But both the Shanty and The Wharf get overrun by drunken tourists pretty quickly. The Wharf does host an industry karaoke night on Sunday, however, which is reason enough to miss your ferry ride home.
Also located in Edgartown, Behind the Bookstore is a coffee shop during by day and a chill outdoor scene by night (think twinkle lights and strong cocktails). This spot is perfect if you have a big group for dinner and would rather sit around a table than shout over each other at a loud bar. While the ambiance is better (and the money more worth it) at night, they also offer a good upscale brunch, if you’re looking to be a little bougie. Speaking of bougie, if you’re lucky enough to be invited by a member, the Edgartown Yacht Club hosts the best summer dances on the island. If not, be sure to still check out their annual sailing regattas.
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(Photos via Getty)
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