In the late 1800s and early 1900s, the waterfront area of Westchester County, New York along the Long Island Sound was the site of a growing collection of recreational developments, including hotels, resorts, and "amusement areas." Local residents concerned about what a County report described as "unsavory crowds" induced the Westchester County Park Association to purchase two existing theme parks, Rye Beach and Paradise Park, and planned a local-government-sponsored amusement park in their stead.

Frank Darling, a veteran park manager with experience at Coney Island and the British Empire Exhibition at Wembley, was hired to design and run the new park, called Playland. Construction commenced in September 1927 and was completed in six months. A design firm was commissioned to decorate the entire park in the Art Deco style.
The park began operation on May 26, 1928. The original design included a boardwalk, ice-skating rinks, a swimming pool, and two beaches, as well as amusement park rides, some of which are still in use.
Built in 1929, the Dragon Coaster serves as the park's mascot and appears in the Playland logo.

The Dragon Coaster is one of roughly 100 wooden roller coasters still in operation in the United States.

Playland was declared a National Historic Landmark in 1987. There is no charge for admission, but "fun cards" or wristbands must be purchased to go on rides. There is a seven dollar charge for cars in the parking lot. According to its website, "Playland also offers free entertainment and has a great beach, swimming pool, boardwalk and pier on scenic Long Island Sound, lake boating, picnic area, mini golf and indoor ice skating."
It is home to a "Grand Carousel". Playland is also home to one of only three "Derby Racers" still in existence. The Derby Racer is not a carousel for the faint of heart as it rotates at 25 miles per hour - three times the speed of a normal carousel. The horses move back and forth as well as up and down, simulating a true gallop as it races around the track. The other "Derby Racers" are located at Cedar Point, in Sandusky, Ohio; and Blackpool Pleasure Beach, in Blackpool, Lancashire, United Kingdom.

Until the beginning of the 2002-2003 NHL season, the New York Rangers hockey team practiced at the Playland ice-skating rink. Ever since the Rangers left, the hockey team from Manhattanville College, located in nearby Purchase, New York, plays its home games at Playland.


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