I knew I’d love Martha’s Vineyard before I’d ever stepped foot on the island. The charming seaside houses, the sailboats in the harbor, the preppy New Englanders, the lobster rolls. The island—which is an easy direct flight from DCA—is more charming in real life than in the pictures. It’s now on the top of my go-to list of summer destinations.
Martha’s Vineyard is divided into four towns: Oak Bluffs, Edgartown, Tisbury, and Vineyard Haven. It’s best to pick a town that suits you and stay awhile—transportation on the island is not easy—nor should it be necessary. We stayed in the tourist-friendly Oak Bluffs, which is lined with Hansel & Gretel style cottages in bright colors with fairytale detailing. It was perfect for our first visit to the vineyard. That said, when I return, I’ll plan to stay in Edgartown, which is filled with houses with white picket fences and chic boutiques.
Below you’ll find all our Bitch-approved recommendations for dining, shopping, and brunching in Edgartown and Oak Bluffs. For other Martha’s Vineyard content, be on the lookout for our of preppy summer fashion inspired by Summercamp Hotel tomorrow and catch our brunch review of The Christopher.
There’s hardly a hotel more fun than Summercamp, which is inspired by its namesake and takes its theme seriously. The charming hotel, designed by Lark Hotels, is filled with cheeky nods to seaside summer camps. There’s a game room filled with Jenga, Clue, and other games and a front porch with fun rocking chairs and lounge seating. Rather than a restaurant, Summercamp has a canteen, filled with doughnuts and snacks and even YooHoos and other nods to childhood favorites. The typical hotel staff are replaced by camp counselors complete with tshirts, whistles—and the cluelessness of a typical 18-year-old camp counselor. We loved staying in the enormous, cheeky hotel located right on the harbor in Oak Bluffs—it made for the perfect first visit to the Vineyard. 70 Lake Ave, Oak Bluffs, Martha’s Vineyard.
The charming boutique hotel, The Christopher’s decor is New England prep meets Caribbean cool, resulting in a bright and beautiful boutique hotel in Edgartown. The posh, luxury hotel is perfectly situated between the shopping and the beach in Edgartown—and we’ll be making our reservations early for our next visit to the vineyard, as this spot books up quickly. 24 S Water St., Edgartown, Martha’s Vineyard.
Among the Flowers Café
This charming indoor-outdoor café serves breakfast, lunch and dinner and is an easy go-to for all of the above if you’re staying in Edgartown. What an adorable spot for coffee or lunch.
17 Mayhew Lane, Edgartown, Martha’s Vineyard.
Back Door Doughnuts
We had heard amazing things about Back Door Doughnuts, a bakery in Oak Bluffs. So we departed early on a weekday and queued up in the long line among other people who had heard amazing things about the bakery. It was worth the wait, as we scuttled out of the tiny bakery brandishing our iced coffees and our enormous box of classic doughnuts.
While the glazed, chocolate covered and vanilla cream doughnuts were absolutely amazing, nothing will compare to the apple fritters. These fried pastries were cinnamon-sugar heaven with chunks of fresh apples, fried and glazed to perfection. Not to mention they were literally the size of your head. I will dream about these pastries for years to come. Open 6 a.m. to 4 p.m. 5 Post Office Square, Oak Bluffs, Martha’s Vineyard
Behind the Bookstore
This charming café serves breakfast, brunch, lunch and coffee—order up and then take your seat. We dropped by for Matcha lattes and pastries after our visit to the bookstore. We loved watching the rain fall under the tree-lined, covered patio. Open 7 a.m. to 11 p.m. 44 Main Street, Edgartown, Martha’s Vineyard.
We dropped by the Christopher for an early brunch before shopping in Edgartown and could not have enjoyed this charming breakfast more. The bite-sized plates were made in-house and served buffet style. We loved the inventive chocolate chip banana bread, chocolate-covered bacon, and perfectly portioned, lemon-y Eggs Benny. Read our full review here. 24 S Water St., Edgartown, Martha’s Vineyard.
While Oak Bluffs is family friendly, Edgartown is loaded with posh boutiques and charming cafes—it’s a bit more adult. Take a stroll down Main Street, which is loaded with preppy staple boutiques like In the Pink, J. McLaughlin and Jack Wills, as well as more trendy boutiques like Slate and Edgar. If you’re a snob with your boutiques—and I am—head directly to Slate and Edgar.
Black Sheep Marketplace
This charming market is perfect to pick up cheese and light snacks if you find yourself of need of sustenance before or after shopping. 18 N Summer Street, Edgartown, Martha’s Vineyard.
We were fortunate to stumble upon the opening party for Edgar, a posh boutique from LA nestled into a charming little seaside house in the middle of Edgartown. The party was a ball, with flamingo float cocktail holders, cheese and charcuterie, and plenty of rosé. While we thought were there just to crash the party, none of us left empty handed, as the selection of unique, stylish pieces was too good to pass up.
There’s nothing I love more than a charming, independently owned bookstore, and Edgartown Books is just that. The two-level bookstore, built into a darling white farm-style house, is packed to the brim with great novels and non-fiction organized perfectly. Plus, there are thoughtful local gifts—as well as newspapers and magazines to read like a local. Be sure to go the charming café, appropriately titled Behind the Bookstore, to have a coffee and read your new purchase. 10 a.m. to 10 p.m. 44 Main St, Edgartown, Martha’s Vineyard.
In the Pink
Because no trip to the seaside is complete without Lilly Pulitzer, be sure to drop into In the Pink to pick up the latest and greatest Lilly print. Other seaside staples, like J. McLaughlin and Island Outfitters, are conveniently right around the corner. 33 Main Street, Edgartown, Martha’s Vineyard.
Nestled into a charming cottage, Slate is stocked with some of my very favorite brands for clothes, shoes, and accessories including: Splendid, Rebecca Taylor, Soludos espadrilles, Marysi a bikinis, as well as tons of stylish, correct womenswear brands for clothing and accessories. I could spend hours—and thousands of dollars—in this boutique. Number 11 North Summer Street, Edgartown, Martha’s Vineyard.
This cute women’s boutique has affordable summer fashions for all styles. 41A Main Street, Post Office Box 177, Edgartown, Martha’s Vineyard.
There are two types of dining on Martha’s Vineyard: divy little seafood joints—most of which are nearly impossible to differentiate—and a few European-inspired upscale establishments. We tried our hand at quite a few seafood spots—ensuring we try the oysters and lobster rolls at each one, in the name of research. The gluten-averse and health conscious will also appreciate that in addition to sandwiches, fried fish, and fried everything, many of these spots also served sushi. And it was good sushi. I wouldn’t have expected that from a New England beach town but perhaps they’ve realized their waspy clientele likes to watch their waist lines.
We also enjoyed two Obama-approved fine restaurants: The Sweetlife Café in Edgartown and Lambert’s Cove in West Tisbury.
We didn’t know what to expect with Beetlebung, an oddly named fusion restaurant on the main drag of bars and restaurants in Oak Bluffs. It ended up being the absolute perfect spot for a girls’ night out, with creative cocktails and shareable Asian fare. The food is creative and fun, with local fish tacos, lobster sliders and more. The cocktails are made with local herbs and fruits—I went girly with a fresh raspberry mojito crush that was as light, refreshing and fun as it sounds. We shared the Beetlebung drunken noodles, made with Thai rice noodles, basil, chil, garlic and added hot buttered lobster claws It was phenomenal. Never turning down lobster, we also shared the pan-seared local scallops served atop a lobster tabouli with a tomato bacon confit. Definitely add this quirky, creative resto to your to-do list. Open 8 a.m. to 11:30 a.m. 53 Circut Avenue, Oak Bluffs, Martha’s Vineyard.
An upscale farmhouse inn and restaurant, Lambert’s Cove reminded me of the restaurants I’ve visited in Southern France—a beautiful old, white farmhouse surrounded by well-kept gardens on acres and acres of farmland. Inside, the decor is traditional Victorian—with lots of Persian rugs, Mahogany furniture and leather-bound books. The restaurant is located in the atrium, with the white table clothes and impeccable service you’d expect from such an establishment. We enjoyed the seasonal, American fare—with chicken, steak and fish on the fairly traditional menu. It was a wonderful dining experience and should be added to your list of fancy date night spots while on the vineyard. 90 Manaquayak Rd, Vineyard Haven, Martha’s Vineyard.
Lobsterville Bar & Grille
As soon as we arrived in Oak Bluffs, we dropped our bags and made our way to the bar for dockside oysters and white wine—and catch up time. The oysters and wine hit the spot—as did the mini lobster rolls and the Bang Bang shrimp, which I devoured without sharing. 8 Circuit Avenue Extension, Oak Bluffs, Martha’s Vineyard.
Location, location, location, as they say. As the name implies, Lookout Tavern’s proximity to the beach could not be more perfect for afternoon cocktails in your swimsuit. The two-level wooden tavern is lively and friendly—grab a seat at the bar overlooking the ocean or on the shaded picnic tables. The drinks are cold and the food is great. Lookout Tavern earned the well-deserved award for best lobster roll in town and the sushi is great, too. 8 Seaview Ave., Oak Bluffs, Martha’s Vineyard.
Sand Bar & Grille
The Sand Bar & Grille is a festive, tropical restaurant with a straw hut for a bar, tiki torches and sand under your feet. There’s fried food, an epic lobster roll, and tropical drinks. The service was appropriately slow on our visit—they must be on island time. 6 Circuit Ave. Extension, Oak Bluffs, Martha’s Vineyard.
Of all the restaurants we visited, the Seafood Shanty was the fan favorite! While Edgartown is more posh than Oak Bluffs, we were pleased that it boasted its own seafood joints. The three-level Seafood Shanty is a lively bar and restaurant with an enormous roof deck overlooking the harbor.
We settled in under an umbrella for happy hour of fried shrimp, oysters, white wine and lobster rolls. The tunes were good, the service friendly, and everyone was having a ball—we were tempted to stay all night. A must-visit in Edgartown. 31 Dock Street, Edgartown, Martha’s Vineyard.
The Sweetlife Café
Built into a stunning restored Victorian home, the Sweetlife Café is utterly charming and perfect for a romantic dinner (which is why the Obamas had date night there!) You can sit inside in the Victorian living room, or outside under the string lights, and we chose the latter. The cuisine is inventive American fare, with a focus on local ingredients. We did a pretty predictable order, sharing a bottle of Sancerre, tuna tartare, beets and burrata, and scallops between the three of us. I’ve eaten quite a lot of tuna tartare and beet salads in my day, and these were probably some of the best iterations I’ve sampled to date. The tuna was prepared in the classic fashion, but with a truffle ponzu and crispy yucca fries. It was heavenly, as where the beets, served with creamy burrata and toasted pistachios. I will say that the portion sizes were relatively small—we wished there were more of everything—and the prices rather steep, but that’s the name of the game on the vineyard. Sweetlife serves dinner 7 days a week beginning at 5:30 p.m. Reservations recommended. 63 Circuit Ave., Oak Bluffs, Martha’s Vineyard.
BitchBiz: We were hosted by Lark Hotels to stay at Summercamp Hotel. That means this visit was on the house. This article was written independently by Bitches Who Brunch.