The well-known NYC architectural firm Walker & Gillette and landscape architect Gilmore D. Clarke were commissioned to produce a comprehensive design of both buildings and grounds, making Playland the first planned amusement park in the country.

Rides that were operating on Playland's opening day included the Grand Carousel, Derby Racers, The "Original" Whip (there is a historic sign referencing its 1928 creation) and the Dragon Coaster.

In 1966, a major fire at the amusement park claimed some of Rye Playland's all-time classic attractions, including the original Bumper Car ride and the "Magic Carpet" Funhouse.

[9] Until the beginning of the 2002–2003 National Hockey League season, the New York Rangers practiced at the Playland Ice Casino.

Currently, as of 2023[update], the hockey team from Manhattanville College, located in nearby Purchase, plays its home games at Playland.

[10] In 2012, Hurricane Sandy claimed parts of Playland's boardwalk, flooded and caused substantial damage to the Ice Casino, and scattered debris throughout Read Sanctuary.

[11][12] In May 2016, the Westchester County Board of Legislators voted 13–4 to give control of the park to a management company called Standard Amusements.

At the center of this arcade, a Spanish Revival bathhouse and pool terminates the automobile approach along Playland Parkway and its twin towers frame a view of Long Island Sound.

An entrance plaza with central fountain at the beach end of this axis is defined by corner pavilions and anchored by a casino and ice rink building.

The axial mall is flanked by colonnades which serve to visually organize the various rides, games, and restaurants on each outboard side.

Its boathouse consists of two pavilions symmetrically flanking a central colonnade, facing a terrace and boat dock and the lake.

The Grand Carousel contains designs including those on the horses that are completely hand-carved and painted by Charles Carmel from Brooklyn, New York.

The horses possess many unique traits that include elaborate "fish scale" blankets, inlaid gemstones, armor and lolling tongues on several.

A renovation to the main ice rink that included a new surface, boards and glass was completed in 2007 for the Empire State Games.

The Westchester County Police provides law enforcement services throughout the year, but the park is only officer-patrolled on a 24-hour basis from April to October.