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.

Oak Bluffs Mass is located in the northern shore of Martha's Vineyard, an island 20 miles long and 10 miles wide situated five miles south of the southwest tip of Cape Cod. Oak Bluffs is bordered by Nantucket Sound on the north and east, Edgartown on the south, and Tisbury on the west and northwest.