For two centuries after the arrival of the first English on Martha’s Vineyard in the 1640s, Oak Bluffs was a pleasant, but indistinguishable part of Edgartown, best known as a place to collect huckleberries. In the summer of 1835, however, nine canvas tents were pitched in a “grove of enormous oaks” behind East Chop, and members of the Edgartown Methodist congregation moved in and prayed, among other things, that it wouldn’t rain. They chose the site not only for its remote location and lovely trees, but in the hope of attracting fellow believers from Nantucket and the South Shore of Cape Cod.
It worked. By 1842 there were forty tents. By 1851 there were a hundred tents. By 1859 there were 250 tents. On “Big Sunday” in 1860, there were twelve thousand believers in the grove, attending 36 simultaneous prayer meetings. Perhaps most remarkably, from the very beginning, people of all colors and races were welcome in the grove.
By the 1870s some of the tents had transubstantiated into wood. Because of the layout of the campground, however, the new cottages weren’t much bigger than the tents they replaced, though they usually had a second floor, often with a balcony. Local carpenters worked through the winter creating ornate and unique trim that, along with the nearly universal use of Gothic and Romanesque arched windows, gives the tiny buildings their signature fairy-land look. Local businessmen knew a good thing when they saw it and developed the acres surrounding the campground similarly.
According to The New York Times in 1873:
No description can give a correct idea of this city of cottages, for such it is. The idea of the secular company was to furnish a residence at the sea-side, with all its beauties and comforts, at a cheap rate. The city began with tents. Small cottages, cheap and plain, followed. Within four years, 1,000 cottages have been erected of all styles and costs, Swiss, Italian, Romanesque, and English, plain as a barn and gaudy as a Chinese pagoda. These cottages crowd on each other, and families must keep peace from necessity. They cost from $400 to $12,000.
In addition to the cottages and churches there were more than a dozen large hotels and restaurants, a massive croquet ground, miles of boardwalks, nightly concerts and dances, hundreds of bathhouses along the beach, and the Flying Horses Carousel, which was brought up from Coney Island.
Some things have changed, including the name of the town, which was originally incorporated as Cottage City in 1880 and renamed Oak Bluffs in 1907. The road that ran from “Cottage City” to Edgartown is gone, as are the croquet grounds and the beach houses. But most of the town is remarkably intact, making it endlessly photogenic.
“Settled” (as Edgartown): 1642
Incorporated as Cottage City: 1880
Incorporated as Oak Bluffs: 1907
Land Area: 7.4 square miles (19 km2)
Water Area: 18.6 square miles (48 km2)