The liveliest of the Vineyard towns, Oak Bluffs is busy in the summer, peaceful in the winter, and vibrant all year round. This eclectic enclave is home to everything from serene beaches to bustling bistros and some of the Island’s quirkiest and most beloved sights.
Once the site of a prosperous whaling industry, Oak Bluffs was reinvented as a resort town when the need for whale oil declined. The town was originally called Cottage City for the rows of gingerbread-type cottages built by former residents and gained its current name when it was again reincorporated as Oak Bluffs in 1907. Those gingerbread houses are actually an architectural style called Carpenter Gothic, a fascinating format of fanciful scrollwork.
What to Love
- Creative, bohemian vibe
- Carpenter Gothic architecture
- Vibrant culinary scene
- Trendy boutiques
- Lively festivals and community events
People & Lifestyle
Of all the towns on Martha’s Vineyard, Oak Bluffs boasts the greatest number of year-round residents, and there’s plenty to keep them occupied. With four public beaches and the Vineyard’s largest marina, it’s clear this hip town loves its water — residents can typically be found boating, kayaking, swimming, hiking, or lounging on the sand. Art galleries and artisan boutiques are a big scene in this trendy town, and if residents aren’t making the art, they’re buying it. The long list of creative festivals, along with the excellent schools, makes Oak Bluffs an ideal spot to settle in. Preferably in one of the gingerbread cottages.
Things to Do
Oak Bluffs really corners the market on festivals. The Tivoli Day Festival is an old-fashioned street fair and block party held every September to celebrate all the hard work of the summer and to welcome the spirit of autumn to the island. Grand Illumination Night is considered the crown jewel of the campground season and is celebrated by adorning the MVCMA campground gingerbread cottages with paper lanterns.
Listed on the National Register of Historic places, the Flying Horses Carousel is the nation’s oldest operating platform carousel. Originally located in New York, it was moved to Oak Bluffs in the 1880’s. This is one of the few carousels that offer the opportunity to catch a brass ring as they ride.
The Oak Bluffs Fireworks show is one of the Vineyards’ major summer events, while the Martha's Vineyard Wind Festival encourages families to bring a picnic and a kite and enjoy a day together outdoors. Legacy Week was created to engage, empower and celebrate the bond and value of the alumni and students from historically Black Colleges and Universities.
In between all the festivities, take some time for rest and relaxation at Inkwell Beach, the setting for a teen movie called "The Inkwell,” or head to State Beach, one of the island’s most popular spots for lounging and splashing.
Oaks Bluffs offers several excellent schools, including:
Martha's Vineyard Regional High School, 9-12, highly rated public school
Oak Bluffs School, PreK-8, top-ranked public school