Oak Bluffs, Martha’s Vineyard, 02557

Oak Bluffs is perhaps the most vibrant destination on Martha’s Vineyard. Home to multiple seasonal ferry ports, Oak Bluffs is easy to access for a day trip from Woods Hole or Hyannis on Cape Cod. This busy summer town is well known for its “Gingerbread” Cottages, Harbor-front dining, shopping, and eclectic food offerings. 

Downtown Oak Bluffs has its own active harbor, and the town offers miles of beautiful beach and pond front. The harbor has a bustling dining and bar scene in-season with a number of restaurants featuring casual oceanfront dining. Just steps away, you will find Circuit Avenue, a classic New England seaside downtown Main Street. Ice Cream shops, restaurants, retail boutiques, art galleries, an arcade and much more can be found along Circuit Avenue. 

Night Owls take note, this is one of only two towns on Martha’s Vineyard that offers nightlife (the second being Edgartown). Don’t miss The Ritz for live music and dancing, and famed Back Door Donuts for a late-night apple fritter. 

Just beyond Circuit Avenue there is an arts district that is home to several art galleries, some are by appointment only, so plan accordingly. Travel out-of-town on Barnes Road and you’ll find Featherstone Center for the Arts, a locally-driven arts center featuring gallery space, and studio space for classes in many art mediums. From ceramics and paper making, to live music and private events, there is programming for all ages at Featherstone. 

Oak Bluffs waterfront offers an abundance of watersports with options even beyond the Harbor. On the Harbor itself, you’ll find options for fishing charters, rental boats and jet skis, and even a Pirate Boat for the kids. Head over to State Beach on Sengekontacket Pond for Stand Up paddleboard and kayak rentals.

You are always walking distance from the beach in downtown Oak Bluffs, Owen Park overlooks Oak Bluffs Town Beach and nearby Inkwell Beach, and both public beaches make for a great place to take a dip and watch the boats come in and out of the Harbor. State Beach is located a few miles down the road and offers miles of barrier beach with the ocean on one side and Sengekontacket Pond on the other. The beach is easily accessible with roadside parking, as well as conveniently located along one of the Island’s most popular bike paths and the Vineyard Transit Authority bus route. 

On your way out to State Beach, you will pass Noman’s, a popular summer destination for dining, drinking, outdoor games, and live music located beside the Island Inn. This is a great place for the whole family, and well-behaved dogs. Feel comfortable showing up straight from the beach and enjoy a summer night on their sprawling lawn. 

If you like golf, Oak Bluffs has a world-class facility and an excellent restaurant at Farm Neck. This course has hosted a number of celebrities including President Obama. Farm Neck Golf Course stretches through rural seaside farmland with holes abutting Sengekontacket Pond, a breathtaking place for a few rounds. 

Oak Bluffs is well known as a cultural melting pot, and is home to important historical monuments like the Shearer Cottage, an institution for over one hundred years. Shearer Cottage was featured in the Green Book, and catered to African American guests in a time when they were not welcomed at many establishments. Shearer Cottage is part of the African American Heritage Trail in Oak Bluffs. Inkwell Beach is another historic place where African American families have safely and proudly gathered for generations. 

The “Gingerbread Cottages” of Oak Bluffs are located at the Martha’s Vineyard Camp Meeting Association, within walking distance of Circuit Avenue, the harbor and the ferry terminals. This enclave of brightly-colored homes has been a draw for visitors of all ages for generations and was once the namesake of the town, “Cottage City.” In the early 1800’s, a group of Methodists started holding regular meetings on this site. It grew into a seasonal community of fancifully ornate summer cottages centered around a Tabernacle that still operates as a meeting place and holds public church services. The Cottages are home to the annual August “Illumination Night” every August, an event dating back to the late 1800s in which all of the homes are covered with Japanese-style lanterns, and every home lights them simultaneously. The lighting is preceded by a performance from a big band in the Tabernacle and provides a breathtaking sight that you just won’t find anywhere else and one that you will never forget!

Another beloved historic landmark is the Flying Horses Carousel, the nation’s oldest platform carousel. Since 1884, the Flying Horses Carousel has delighted visitors in the town of Oak Bluffs, where children and adults can ride ‘round-and-‘round and try their luck at the coveted brass ring.

For those looking for a little bit of everything, within walking distance to the ferries and easily accessible to the rest of the Island via public transportation, Oak Bluffs is the place for you.

Funded, in part, by the Massachusetts Office of Travel and Tourism.