Peekskill is a 19th-century Hudson River city at the northwest corner of Westchester County. The city plan is based on an orthogonal grid where north-south streets run parallel to the river and the natural slope of the land.  East-west streets run perpendicular to the river and slope steeply.

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The new Middle School was constructed on the site of an existing 1920s building, converted to a middle school in the 1960s.  The 1920s building abutted Ringgold Street, a residential street on the uphill side of the site.  To the west of the old school's playing field, there was an 80-foot change of grade down to commercially-zoned Washington Street   The new school was built on this west-facing slope so that the old school could remain operational during construction.  After the new school was completed, the original school was demolished and a new city green was constructed in its place.

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The city plan, the Hudson River Valley, the precipitous slope of the site, and the requirement to preserve the old school during construction of the new one all contributed to the design of the new city green. This green, which is the playing field for the school, responds directly to the city plan grid and to the fabric of the residential neighborhood.