This triangle-shaped island — sitting about 8 miles off the coast of Cape Cod, Massachusetts — has been a secret summer hideaway of the rich and famous for more than a century. Today, the "Hollywood East" reputation is going strong — thanks to frequent visitors like President Barack Obama, David Letterman and Bill Murray, among many others. But despite the all-star summer lineup, a laid-back lifestyle rules the island. The main draw rushing Vineyard visitors off the ferry is the chance to let their hair down for a long weekend. Sure, you'll find insanely expensive summer cottages, and a pricey dining atmosphere to match, in some corners of the town of Chilmark. But low-key towns like Vineyard Haven and Menemsha are still predominantly focused on their marine industries and offer a more casual experience. Even the island's must-have souvenir — a Black Dog sweatshirt — is informal. So swap the stilettos for your scrappiest flat sandals, and do play it cool when you spy some film stars in Edgartown; everyone deserves a slice of a Vineyard vacation.
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Martha's Vineyard is famous for its lack of fast food restaurants (you'll have to go to the mainland if you're craving Starbucks or McDonald's). But with all of the delicious seafood and locally grown produce populating the island's eateries, you won't miss those takeout menus. In fact, you'll eat very well.
If the thought of a Starbucks-less vacation sends you into a spiral, don't worry: There are plenty of breakfast spots on the island that can fulfill your daily caffeine and pastry fix, including Espresso Love. For a bigger menu and a unique dining atmosphere, head to The Right Fork Diner. Situated on the Katama Airfield in Edgartown, the diner offers unobstructed views of the biplanes taking off and landing, making it a popular spot for families.
When you're ready to sample some of the island's marine bounty, critics and locals agree: Larsen's Fish Market should be your No. 1 stop. Sitting pretty in the fishing village of Menemsha, Larsen's offers some of the freshest lobster and oysters in town. And if you're craving lobster rolls, you won't have a hard time finding them. For the best deal, head to Grace's Episcopal Church in Vineyard Haven. On Fridays, the church offers a lobster roll, chips and a beverage for just $18, with proceeds going to local nonprofits (in comparison, most rolls cost $20 or more). Offshore Ale Co., a restaurant and brewery in Oak Bluffs, is well-known for its East Chop Lighthouse Ale and casual atmosphere (go ahead, throw those peanut shells on the floor), but it's also home to one of the island's best lobster rolls. And, of course, no visit to the Vineyard would be complete without a stop at Black Dog Tavern. Considered by many to be an island institution, this waterfront eatery is just steps from the main ferry and features some of best casual seafood dishes in town. Don't leave without trying the quahog chowder.
In the mood for something a little more formal? The vineyard has you covered there, too. The Port Hunter (try the raw bar) and State Road (try the scallops) are both worth the hype, according to recent visitors. And when you're ready to let loose and dance with some locals, head to The Ritz, a legendary dive bar in Oak Bluffs that features live music and karaoke.
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