The Flying Horse Carousel, built around 1876, should not be confused with Martha’s Vineyard’s Flying Horses Carousel. Both were manufactured by the Charles W. F. Dare Company, one of the leading amusement manufacturers at the time, and both contend to be the oldest continually operating carousel in the country.

Watch Hill’s carousel was never meant to end up in the coastal village; it was part of a traveling carnival, which abandoned it in Westerly in 1897. It was powered by a calico horse until 1897, when the horse was replaced by waterpower. Since 1914, the carousel has been operated by electricity. The ride was seriously damaged in a 1938 hurricane, but luckily all the horses were recovered from nearby sand dunes. 

Like a few other antique carousels in the United States, the Flying Horse has a device holding metal rings that lowers midway through the ride. Riders can grab the rings as they pass by. The last ring, made of brass, granted riders a free ride. Restorations and improvements have occurred over the years. The carousel is currently maintained by the Watch Hill Improvement Society.