There are six distinctive towns on the Vineyard, each with its own character and appeal, and locals generally divide the Island in two: up-Island and down-Island. The “down-Island” towns refer to the eastern towns of Tisbury, which includes the year-round harbor port of Vineyard Haven, Oak Bluffs, and Edgartown, each vibrant port communities, very unique from one another, very easy to walk around and very easy to get between. Then there are three rural towns on the west side which constitute “up-Island” including West Tisbury, Aquinnah, and Chilmark, which offer a more pastoral landscape, dotted with small farms and cozy shopping in a bucolic setting.
We always recommend visitors take a ride up-Island to truly appreciate the size, scope, and natural beauty of Martha’s Vineyard. Up-Island is most easily accessible via car, though many avid cyclists make the trip on bike, and the local bus service and sightseeing tours offer options for getting up there two. If you only have a day, here’s what you want to try to see.
The Cliffs at Aquinnah and Gay Head Lighthouse
Commonly referred to as the Cliffs, the stunning Aquinnah Cliffs are protected as a National Historic Landmark and are a sight to behold. If you only make one stop up-Island during your visit this should be it. On a walk up to the cliffs, you’ll pass several souvenir shops and snack bars, as well as a casual sit-down restaurant: the Aquinnah Shops Restaurant. Make your way to the scenic overlook and you won’t believe the magnificent view of the cliffs and the lighthouse. It’s the most popular place to take a photo on Martha’s Vineyard, but even with the best camera the picture can’t do it justice. And while you're there, head to the nearby Gay Head Lighthouse, atop 130-foot cliff, which is open daily in season for tours to the top.
Up-Island beaches are often considered the most stunning and most pristine on the Island, they’re also generally less crowded. If you happen to visit after mid-September and before mid-June you’ll have full access to the shore, as many of the Island’s most beautiful beaches become resident only beaches in the summer. Some of the best ones to explore include Lambert’s Cove Beach in West Tisbury, and Lucy Vincent and Squibnocket Beach in Chilmark. Moshup Beach in Aquinnah takes the cake and is often named among the nicest beaches in the world. It’s open year-round to the public and is arguably the most scenic on the Island thanks to views of the stunning Gay Head Cliffs. At times, Moshup has very large waves, making this a popular surf-spot on the southern and western end of the island.
Restaurants and food establishments are harder to come by in general up-Island but there’s still delicious bites to be had. The Chilmark General Store is a popular place to grab a slice of their famous pizza, intended to be enjoyed on their large porch which often becomes a common place for celebrity sightings. Nearby is Chilmark Chocolates, arguably the best chocolate on Martha’s Vineyard. The store keeps limited hours so if you pass by and it’s open you’re in luck and you must stop. If you’re visiting on a Wednesday or Saturday in summer you’ll want to take a tour of the West Tisbury Farmer’s Market which has been operating rain or shine since 1974, making it Martha's Vineyard's oldest, largest, and most delicious open-air market. Local farmers and food purveyors sling their wares and their produce, and you can’t find a fresher shopping experience on-Island. For the freshest seafood head to Menemsha, a quaint fishing village in Chilmark, known for its stunning sunsets and New England charm. Menemsha and Larsen’s Fish Market offer a variety of prepared seafood meals that can be enjoyed on the nearby beachfront with a front row to an unobstructed sunset over the water. Sandwich lovers want to make a point to stop at 7a Foods in West Tisbury, a popular “farm to take out” spot that makes some of the best food on Martha’s Vineyard, including their famous Liz Lemon sandwich, Hot house-made pastrami, turkey, swiss, coleslaw, Russian dressing and potato chips on rye.
Martha’s Vineyard is home to over 40 working farms and many of them can be found up-Island. Grey Barn Farm in Chilmark is a beautiful, certified organic farm that offers fruits vegetables, grass fed beef, and awards winning cheese in their farm stand. Take a walk around the grounds and check out the animals grazing while nibbling on one of their tasty cheeses. Another popular and picturesque farm that is open to the public is the Allen Farm, Martha’s Vineyard’s oldest continuously working family farm, the Allen Farm on South Road in Chilmark is made up of 100 acres of rolling pastures and meadows lined by historic stonewalls, overlooking Chilmark Pond and the Atlantic Ocean. The family’s environmental commitment is reflected in their farm products, from the taste of the grass-fed lamb to their intricate hand-woven woolens. For a map of all the Island’s farms click here.
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