Oak Bluffs was first settled in 1642 and was officially incorporated in 1880 as Cottage City, Massachusetts. Before its incorporation, it was part of Edgartown. The town re-incorporated in 1907 as Oak Bluffs. Oak Bluffs originally began as the center for tourism on the Vineyard. While the other towns were more focused on industry, Oak Bluffs became a Mecca for travelers from around the world as early as the beginning of the 1800s. It also became a center of the thriving 19th Century Methodist movement.In 1835 this community served as the site for annual summer camp meetings, when Methodist church groups found the groves and pastures of Martha's Vineyard particularly well suited to all-day gospel sessions.
Wesleyan Grove, as the Oak Bluffs Camp Ground was called, rode the crest of the religious revival movement. By the mid-1850s, the Sabbath meetings here were drawing congregations of 12,000 people. They came for the sunshine and sermonizing in hundreds of individual church groups.
Each group had its own communal tent where the contingent bedded down in straw purchased from local farmers. Services were held in a large central tent. The communal tents gave way to "family tents," which reluctant church authorities granted only to "suitable" families. But the vacation urge could not be checked. Family tents turned into wooden cottages designed to look like tents. And the cottages multiplied, trying to out-do each other in brightly painted fantasies of gingerbread. A new, all-steel Tabernacle structure replaced the big central tent in 1879. It stands today as a fine memento of the age of ironwork architecture.
Within 40 years of the first camp meeting here, there were crowds of 30,000 attending Illumination Night, which marked the end of the summer season with stunning displays of Japanese lanterns and fireworks.
Wesleyan Grove struggled to hold its own against such secular attractions as ocean bathing, berry picking, walking in the woods, fishing, and croquet playing. There were efforts to ban peddlers, especially book peddlers. A high picket fence was built around the Camp Ground proper. By the 1870s, Wesleyan Grove had expanded into "Cottage City" and Cottage City had become the town of Oak Bluffs, with over 1,000 cottages.
Steam vessels from New York, Providence, Boston, and Portland continued to bring more enthusiastic devotees of the Oak Bluffs way of life. Horse cars were used to bring vacationers from the dock to the Tabernacle. The horse cars were later replaced by a steam railroad that ran all the way to Katama. One of the first passengers on the railroad was President Grant. The railroad gave way to an electric trolley from Vineyard Haven to the Oak Bluffs wharves, and the trolley eventually gave way to the automobile.
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