How to navigate 20 beautiful miles of lobster rolls, cocktails, fried fish, donuts, and more.
LessIn a space just off Main Street in Edgartown, this is arguably the best raw bar on the Vineyard—which is something we don’t say lightly. They usually serve oysters fresh from the waters around the island, with a few bright PEI bivalves thrown in, along with dishes like lobster roll sliders topped with caviar, fresh and creative crudo, and wet- and dry-aged steaks. The patio that’s tucked away behind greenery will be your favorite hang all summer.
The origin story of Back Door Donuts is that people would stop by Old Stone Bakery late at night (and maybe after a few drinks) and beg for donuts. So in 2018, they opened this late-night donut spot. Everything is very good, but the apple fritters are the best thing they do. Plus, the line outside the shop is its own kind of fun hang, with everyone full of fresh seafood and booze.
So, you’re on Martha’s Vineyard, it started raining, and you’re simply not trying to get soaked while on vacation. When that happens, hit up this sprawling all-day spot with excellent sweet chili and tandoori chicken wings, mussels in curry sauce, pizza for kids (and your friends who eat like children), and a strong beer list. You’ll be able to occupy yourself with a few games on the 10-lane bowling alley or catch up on the Yankees or Red Sox scores on the TVs throughout the bar.
We’re not going to apologize for the number of sunny rooms with good cocktails and fresh bivalves on this list, and Beach Road is our favorite spot for this situation in Vineyard Haven. The big dining room overlooks Lagoon Pond, and you’ll want to make a reservation (or luck into a bar seat) for a proper spread of oysters, pasta piled high with sweet lobster meat, and delicious cocktails like the Ginja Ninja (mezcal with ancho reyes, carrot juice, turmeric, and lime).
Get up early, and take the ferry over to Chappaquiddick for an adventure, which should include stopping at the Mytoi Japanese Garden to feel one with nature and have some pond time. When you’re done, Atlantic Fish and Chop House is waiting for you right in Edgartown with waterfront seating and harbor views. It’s not super stuffy, but the energy is resort casual—think heavy on the loafers and linen—and you’ll have a slew of great options for seafood and whole fish.
Head to the Vineyard’s VFW hall for a non-New England take on seafood, which is a little like going to Paris and skipping the Louvre, but we’ve done that too, so no judgment. Jamaica-born chef Deon Thomas and his wife Emily have been serving a rotating menu of jerk or blackened salmon, zesty island kale soup, conch, plantains, and more in this relaxed space for years, and there’s often live music in the evenings. If Deon’s famous jerk chicken is on the menu, get it, and get it spicy.
This Chilmark favorite has been open since 2008—it’s a farm, it’s a bakery, and, yes, it’s got fresh cheese. Visit and you can stock up on freshly baked bread, sweet treats, orange rind-covered Prufrock cheese, milk, preserves, and meats raised right on the farm. Swing by and stock up on a ton of stuff for your visit to the island, because starting your day with a freshly baked chamomile cream bun or lemon poppy danish is clearly the correct life choice.
There aren’t a lot of places to sit down for a meal in Chilmark, but after a day climbing the Menemsha Hills, unwind with the Tavern’s familiar menu of farm-to-table classics. You’ll find crispy fish and chips, burrata with island tomatoes, and a stellar poulet frites. The locals will probably tell you Chilmark is “the wettest dry town in America,” but the restaurant will hook you up with basic mixers for cocktails. Or, you can just bring a bottle of wine like an adult.
You can’t have an East Coast vacation without a perfect summer shack that serves lobster rolls and fried clams, and the Lookout is the best version of that on the Vineyard. With views overlooking Oak Bluffs, you can watch people file out of the ferry, or just gaze at the ocean while tucking into that aforementioned toasted and buttery lobster roll, alongside fried seafood, raw bar offerings, and a solid assortment of fresh sushi, all available to go.
Cozy Détente is one of the most romantic spots on the island, with a charming outdoor courtyard decked in twinkle lights and surrounded by shingle-covered cottages. They’ve been serving seasonal American classics since 2005, and they have a pretty solid wine list, too. While the menu updates almost daily, past standouts include the local monkfish with lobster bao and sauteed Vineyard shitake mushrooms and crab and corn salad with spiced lavash.