The Magic of Oak Bluffs’ Flying Horses Carousel

A Treasure of Americana

Built by Charles W.F. Dare in 1876, the Flying Horses Carousel holds the distinction of being the oldest operating platform carousel in the United States. It originally spun on Coney Island, New York, and a stamp reading “Coney Island #4” hints at its early history before it was relocated to Oak Bluffs (then Cottage City) in 1884 by F.O. Gordon.

A Stroll Through History

The carousel was purchased by the town in 1889, moved to the heart of Circuit Avenue, and later officially named “Flying Horses” in 1896. In recognition of its cultural and historic importance, it was added to the National Register of Historic Places in 1979 and designated a National Historic Landmark in 1987.

What Makes It So Special

This 20-horse spectacle is composed of hand-carved wooden steeds with original oxidized glass eyes. While their manes are refreshed over time, the craftsmanship of each horse remains intact. The carousel includes a traditional brass ring game, where riders reach out to grab rings from a dispenser during the ride. If you snag the brass one, you win a free ride—a beloved tradition for generations of children and adults.

Though originally powered by steam and even horses, the carousel was electrified in 1900. Today, it’s operated by a 1923 Wurlitzer #103 Band Organ, providing that signature old-timey music that completes the nostalgic experience. The Martha’s Vineyard Preservation Trust restored the ride in 1986, bringing back its vibrant color panels and ensuring its structural integrity.

A Year-Round Family Tradition

For families who live on Martha’s Vineyard and for those who return year after year, the Flying Horses is a must-visit. Generations of children have made their first carousel memories here, and stories of kids who ride every summer, year after year, are not uncommon. Whether you’re local or visiting, the experience never loses its charm. The carousel sits right in the heart of Oak Bluffs, just steps from the ferry and the vibrant shops of Circuit Avenue, making it a central and convenient stop for all ages.

Why the Flying Horses Matters

The carousel connects generations, with grandparents bringing their grandchildren to ride the same horses they once did. In Oak Bluffs, where Victorian gingerbread cottages and family-friendly boardwalk charm define the town’s vibe, the Flying Horses stands as a symbol of continuity and joy. Over the years, it's been a backdrop to birthday parties, engagements, and community celebrations.

Visiting Tips & Insider Info

The carousel opens each year around Memorial Day weekend and runs through early fall, with expanded hours during the peak summer months. For the best experience, try to visit early in the day before the crowds build up. And don’t forget—if you grab that brass ring, you earn another ride, so sharpen those reflexes! You’ll find it at 33 Oak Bluffs Avenue, right at the start of Circuit Avenue. Parking can be limited during the busy season, so plan ahead or arrive early if possible.

You can even host private events here. The Vineyard Preservation Trust offers party bookings for a truly unique and memorable setting.

National & Local Context

Of the handful of 19th-century Dare carousels that still exist, the Oak Bluffs Flying Horses stands out as a platform-style carousel rather than a suspended one, which makes it even rarer. Carousels like this are a vanishing piece of Americana, and its survival and restoration are a testament to the Vineyard community’s dedication to preserving its heritage.

Your Oak Bluffs Real Estate Connection

If you’re drawn to the charm and community spirit of Oak Bluffs—and who wouldn’t be, with timeless icons like the Flying Horses Carousel—the O’Hanlon Group is here to help you find your place. Whether it’s a year-round home or a summer retreat close to the carousel and the heart of town, we’re your trusted Martha’s Vineyard real estate resource.