The short stretch of surface road and low-standard freeway connects Interstate 95 (I-95, named the New England Thruway) and U.S. Route 1 (US 1) with the Playland amusement park in Rye.

During the mid-1960s and early-1970s, the parkway was part of a proposal to create a new bridge across the Long Island Sound connecting Rye to Oyster Bay.

Playland Parkway begins at an interchange with I-95 in Rye, heading southeast as a four-lane divided freeway.

As result of the middle-class belief for the new park, the new parkway was designed so that a similar clientele could come by car to visit.

[2] The new parkway, which was conceptualized as a 15-mile (24 km) roadway, had the section between the Boston Post Road (US 1) and Rye Playland, with construction starting in 1928.

Rutherford Hubbard, the leader of the "Rye Citizens Advisory Committee Against The Sound Bridge" stated that Moses should think about the people and be more democratic about his decisions.

[11] Once opposition started to appear on the Long Island side of the sound, Governor Rockefeller cancelled the project himself on June 20, 1973, seven years after the first proposal was selected.