Many people don’t realize just how big, and just how rural Martha’s Vineyard really is. Martha’s Vineyard is approximately 96 square miles, roughly triangular in shape, 25 miles (42k) at its longest point east to west, and 9 miles (12.8k) at the longest point north to south. Locals refer to the eastern side of the Island as “down-Island” and the western side of the Island as “up-Island.”
There are six distinctive towns on the Vineyard, each with its own character, flare, attractions, dining, lodging and more. The “down-Island” towns refer to 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 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.
Given that most visitors reach the Island by ferry, on boats that arrive into the down-Island harbors, it’s not uncommon for a visitor to spend days on Martha’s Vineyard and never get “up-Island,” or even know that the second half of the Island exists (many locals would like to keep it that way but we’re happy to help spread the news of all the amazing offerings of Martha’s Vineyard!). We definitely recommend you make the time to explore up-Island, we promise you will not be disappointed. And if you don’t have a car you can still make it “up” there via the Vineyard Transit Authority bus system.
Here’s three of our favorite must see up-Island attractions.
The Aquinnah Cliffs
Located on the westernmost edge of the Vineyard, the Aquinnah cliffs are simply breathtaking. This impressive landmark is so exquisite it was recently named the most beautiful place in all of Massachusetts by Condé Nast Traveler. There’s beauty in every direction and breathtaking views of Vineyard Sound and the Atlantic Ocean. 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 Shop Restaurant. Make your way to the scenic overlook and you won’t believe your eyes. 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. Check out the nearby Aquinnah lighthouse, atop 130-foot cliff, which was recently moved back from the edge to protect it from becoming victim to coastal erosion. The lighthouse is open to the public daily from Memorial Day through Columbus Day and is very much worth the fifty-five steps to the top.
Menemsha is a small, classic New England fishing village located in the town of Chilmark, and situated on the northern coast of Martha’s Vineyard. You’ll smell its authenticity as soon as you step out of the car, and you can’t miss the working fishing boats that litter the harbor and the stacks of lobster traps that decorate the streets. A visit to Menemsha is most popular for a summer sunset, when the sun goes down over an unobstructed section of the Vineyard Sound, making for one of the best sunsets on the east coast. Be sure to grab a lobster dinner or some clam chowder at one of the local fish markets, and don’t forget to enjoy a bottle of wine while you wait–many Island towns are dry and Chilmark allows for BYOB.
Open to the public and displaying local artists for over 45 years, the Field Gallery is a fun and easy stop in West Tisbury. A small, indoor gallery displays fine art, and the open outdoor space is home to Thomas Maley's now iconic sculptures, offering guests a great photo opp! Plus, the Field Gallery is right across the street from Alley's General Store, one of the country's oldest general stores worthy of a visit. And during peak season, just down the street at the Grange Hall, is the West Tisbury Farmers Market on Wednesdays and Saturdays, and the Vineyard Artisans Festival on Sundays and Thursdays, making this up-island trip a trifecta of fun!
It's my job to love this place, and it's no work at all.