The Town of Oak Bluffs is a resort town on the northeast shore of Martha's Vineyard.  There was a large pre-Colonial Indian population that took advantage of the fishing and shellfishing in Oak Bluffs, probably on a seasonal basis. 

The explorer Gosnold was among the first European adventurers, fishermen and traders who set up temporary or seasonal camps on Cuttyhunk beginning as early a 1602.  The first grant of 500 acres of land made to a European was in 1642 to John Dagget but it wasn't until 1667 that the first permanent European settlement took place. 

Subsistence farming, fishing and shellfishing supported the early settlers.   In 1835, Jeremiah Pease chose an oak grove on the edge of Squash Meadow for a camp meeting of island Methodists.  The summer meeting became popular and attendance grew like wildfire.  Groups of church members first came to stay in tents for two or three days, then families started bringing their own tents to the weekend retreats. 

In 1835, nine tents were sufficient to shelter the attendees; in 1858, 12,000 people attended the Sunday services.  The camp meetings were ecumenical in spirit and attracted members of most Protestant sects as well as Roman Catholics.  By the late 1850's, annual visitors were replacing tents with elaborately decorated carpenter Gothic cottages and the first major hotel in Oak Bluffs opened in the 1860's.  

The expanding number of permanent residents, including a significant immigrant population of Portuguese, continued a substantial fishing industry, built cottages and serviced summer visitors in the thriving tourist business.  Through the 19th century, Oak Bluffs saw the side-by-side development of a secular seaside resort featuring a trotting track, roller rink and dance hall, and the continuation of a religious summer revival.  

In modern times Oak Bluffs has come to terms with all of the strands in its past, and among the most sought after houses are the small, colorful, carpenter Gothic cottages built by revivalists.