Edgartown is a magical town known for its Jaws-dropping beaches, lighthouses, white clapboard mansions, fabulous restaurants, and stores. From Edgartown, you can take the Chappy Ferry (you might feel like "you're gonna need a bigger boat") to Chappaquiddick island, which offers bikeable beaches and a wildlife refuge. The things to do and see in Edgartown itself are numerous, but if you're looking for something sweet, we recommend stopping by Murdick's Fudge and indulging in their homemade fudge and candies.
Menemsha is a historic fishing village in the town of Chilmark, which is known for its fresh seafood and incredible sunsets. Parking is limited and time-bound (2 hours), but Menemsha is worth the trip. If you come with an appetite, do yourself a favor and stop by Larsen's Fish Market, where you can grab a quick lobster roll, chowder, smoked bluefish, and more.
Oak Bluffs is a colorful and historic town offering many great opportunities for shopping and dining. Be sure to take a walk through Oak Bluffs Campground, which is a National Historic Landmark where you can marvel at the nearby 19th-century Gingerbread Cottages. Oak Bluffs is also home to the Flying Horses Carousel, which is the oldest operating platform carousel in the United States. Finally, if you're willing to wait, follow your nose to Back Door Donuts and partake in the island's best donuts and baked goods.
The Aquinnah Cliffs are one of Martha's Vineyard's most-loved tourist spots. Come here to explore the lower beach paths to see the cliffs up close and stretch along the sands at Moshup Beach. You can also take the upper trails to the top of the cliffs to catch a glimpse of Gay Head Lighthouse and nearby Elizabeth Islands from the Overlook. There are several vendors adjacent to the Overlook, offering souvenirs and light refreshments. Also adjacent to the Overlook is the Aquinnah Shop Restaurant, which offers an amazing view of the ocean and is one of the oldest restaurants on the island. There's parking available (for $15 in the summer), but the lot fills up fast.
The Grey Barn Farm is a certified organic farm, creamery, and bakery located in Chilmark. Open Thursday through Monday, the Grey Barn Farmstand offers a wide selection of baked goods, cheese, meat, and other locally-sourced items. You can't go wrong with anything you try here!
Looking for something a little more upscale? The State Road Restaurant in West Tisbury is a wonderful place to dine after a day of sightseeing. The menu combines seasonal fruits, herbs, and vegetables from the restaurant's on-site garden with other locally-sourced ingredients from across the island. If you're interested, we recommend scheduling a reservation in advance through Resy as they tend to be very busy in the summer months.
A casual and fun gathering place, Oak Bluff's Nomans is an excellent spot to grab a bite to eat or a hangout on the patio with a cold beer or cocktail. No reservations offered here - find a table and order at the counter. For the spirits connoisseurs, Nomans is known for distilling some of the best rum on the island.
The Chilmark General Store is a small community market where you can load up on all of the essentials or grab something a bit more substantial. While best known for their amazing pizzas, the General Store also offers a variety of prepared foods from their take-out counter.