Oak Bluffs

The best of the Vineyard

On the North Shore of Martha’s Vineyard sits the beautiful Victorian seaside Community of Oak Bluffs. Originally settled in 1642 it was named Cottage City and was incorporated in 1880. As the town changed, becoming more diverse and establishing a growing year round population, it was renamed Oak Bluffs in 1907 describing the vision seen as boats brought visitors to the shore.

Oak Bluffs is the home to many historic landmarks such as The Flying Horses, the oldest continually operating carousel designed by Charles W.F. Dare and built in 1876. It is a favorite of young and old alike. The Martha’s Vineyard Camp Meeting Association encompasses over 300 Gothic Carpenter style “Ginger Bread” Cottages that circle the Tabernacle, where every Wednesday in summer for over 120 years, the evening Sing Along takes place. In August for one magical night The Grand Illumination sets the Campground aglow with lanterns and a patriotic concert that is attended by thousands.

The Feast of the Holy Ghost at the Portuguese American Club each year reminds us of the many Portuguese people that settled here and were part of the great fishing tradition on Martha’s Vineyard. Black cultural events have taken place for over 100 years on Martha’s Vineyard and to this day the Shearer Cottages are in business as the oldest continuously black owned family business in the state.


Writers such as Dorothy West and Tom Clancy found Oak Bluffs a stimulating and inspirational place to work. Painters and photographers like Alison Shaw have made Oak Bluffs their home. Arts abound with galleries, studios, art strolls and flea markets. Musical events happen though out the summer such as Musical Mondays at Featherstone Center for the Arts and free band concerts take place at Ocean Park. Several festivals throughout the year invite visitors from far and wide to fly kites, join in bike races, iron man competitions, windsurfing and tournament fishing. A farmers market in Washington Park greets you on Sundays as you drive into town.

Oak Bluffs also offers several free public beaches and parks, fine and casual dining, fun shopping and golfing at Farm Neck. Being the hub of transportation on the island allows for convenient traveling. The shoulder seasons are beautiful in Oak Bluffs and rates will drop as summer fades. Christmas in Oak Bluffs is a step back into simpler times with a tree lighting and band concert. Come visit the magic of Oak Bluffs any time of year, it is waiting for YOU.

The Oak Bluffs Association

Email: oakbluffsassociation@gmail.com

Christine Todd, Executive Director

PO Box 1521,

Oak Bluffs, MA 02557

Phone: 774-563-9197

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