In 1835 the Methodist camp known as Wesleyan Grove (also a National Historic Landmark) was established in the area.

Development of the area as a summer resort became more formally organized with the establishment of the Oak Bluffs Land and Wharf Company in 1866.

Its artwork closely resembles that found in an 1870s catalog published by the Charles W. F. Dare Company, a major manufacturer of carousels in the late 19th century.

At least one expert believes that artwork of the carousel itself was done by the same artist whose work appears in the catalog, suggesting its construction date to be between 1876 and 1878.

The town sold the carousel to Joseph Turnell in 1896, and it then went through a succession of owners before its acquisition by the Martha's Vineyard Land Trust in 1986.

Fourteen spreader panels radiate from the central platform, and are secured to the upper canopy by the columns that also support the horses and carriages of the carousel.

[3] When the site was purchased by the Martha's Vineyard Land Trust, the Flying Horses underwent an extensive restoration, returning the carousel to its original appearance, complete with the historic panel paintings that were done by a Dare Company artist.