Things To Do

Explore Oak Bluffs

There’s always plenty to explore in Oak Bluffs and beyond, no matter the season! As one of Martha’s Vineyard’s principal ports of arrival for summer tourists, the bustling and hustling of Oak Bluffs is always lively and happening. Discover the well-preserved town, while diving from history tours to fun in the sun, every day of the week!

The active Bluffs Harbor offers shopping, dining, and a timeless carousel and arcade. A few minutes stroll from the hotel and you can reach two town beaches and a great area for the live music scene on Circuit Avenue.

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Top 10 Things to do in Oak Bluffs

Ride the Historic Flying Horses Carousel
Take the African American Heritage Walking Tour
Sunbathe on Inkwell Beach
Stroll through the Colorful Gingerbread Cottages
Enjoy yoga with the Alpacas at Island Alpaca Farm
Indulge in donuts after hours at Back Door Donuts
Go ice cream tasting on Circuit Avenue
Play a round of golf at Farm Neck Golf Club
Paddleboard and kayak on Sengekontacket Pond
Take a scenic drive (or bike ride!) to East Chop Lighthouse

For the Foodies

Oak Bluffs is a melting pot of cuisines, where you can find something delicious for everyone in your group! Being that we are on a New England island, seafood is one of the first must-haves - whether you are craving fried clams from Coop de Ville, a lobster roll from Martha’s Vineyard Chowder Company, or raw oysters from The Oyster Bar, Oak Bluffs has a plethora of bites from the sea.

For the meat-eaters, try the steaks at Red Cat Kitchen, and bite into some juicy, wood-smoked meats at Sea Smoke. If you’re searching for something on the lighter side, MV Salads, Nancy’s, and the Pawnee House are delightful!

When we speak of the melting pot of cuisines, we love to showcase the Jamaican eats at Vineyard Caribbean, the Thai and Southeast Asian flavors at Bangkok Thai, and the south of the border dishes from Sharky’s, Dilly’s, and Dos Mas. Wherever you decide to dine in Oak Bluffs, know that you are in for a treat from the hard working restaurant owners that call the island home.

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For the Beach Aficionados

Are you looking to sit by the water and enjoy the island sun? Oak Bluffs is home to some of the best beaches on Martha's Vineyard. Here are some amazing Oak Bluffs beaches you can visit while in town:

Inkwell Beach, with strong links to African-American heritage on Martha's Vineyard, is the beach to see and be seen, relax with friends and family, and soak up the sun.

Joseph Sylvia State Beach, the 2-mile stretch of sandy beach and shallow water that served as a main shooting location in the popular film "Jaws.”

Bend in the Road Beach, where you'll wind calm waters making it one of the go-to beaches for kids to play and adults to relax, with easy parking or a short bike ride from the hotel.

Eastville Beach, with views of the Steamship ferries coming and going, along with Vineyard Haven Harbor, this beach is family and stroller friendly, offering parking on site.

For the History Buffs

Oak Bluffs is steeped in rich history, and you could spend an entire vacation learning, discovering, and exploring this history.

The African American Heritage Trail recognizes the contributions made by people of African descent to the history of the island. Mariposa Museum explores American history and experience through a diverse lens and the creativity of artists, scholars, and other creatives.

The Martha’s Vineyard Camp Meeting Association, with the historic gingerbread cottages within, which are well-known and well-loved for their unique charm, is a local gem that’s perfect for early morning walks with your coffee.

Nearby Flying Horses Carousel is the nation’s oldest platform carousel. Since 1884, the Flying Horses Carousel has delighted visitors in the town of Oak Bluffs. Each horse is brightly painted and fixed to the rotating platform by a metal post. Try your luck at grabbing the brass ring–fun for all ages!