Cypress Street Playground is a historically significant park, comprised of 5.22 acres, considered to be one of the first municipal parks established for playground purposes in the United States. The site is bounded by the main High School building to the west, the Gym and Aquatic Center to the south, as well as the Brookline Hills Green Line MBTA Station. To the east is Cypress Street with neighborhoods beyond and to the north is Davis Ave with additional neighborhood abutters. Greenough Street fronts along the High School and Tappan Street fronts the Aquatic Center and Unified Arts Building.
The playground is a long rectangular space with organized athletic functions towards the High School in the western two-thirds of the park. The park is bisected by a major pathway from Davis Ave to Tappan Street that provides pedestrian access to the Brookline Hills MBTA Station. The western part of the park includes a multipurpose rectangular field with two softball diamonds and one basketball court. The fields are used by High School girls’ softball as their home field, and also currently used by men’s softball, Little League as well as High School and Pop Warner football, High School soccer, summer camps, in addition to other public uses of the field. One softball field is currently lighted. Towards Cypress Street, there is one basketball court and an existing playground that is utilized by the local neighborhood as well as many local pre-schools. The fields are currently irrigated.
In 2017 and 2018, previous scoping sessions began to investigate renovations to the Playground. These studies looked in great detail at the athletic fields and disused the pros and cons of synthetic turf at this facility. In May 2018, Town Meeting voted to approve moving the renovations of the Playground forward, but did not approve the use of synthetic turf. In December 2018, a new Design Review Process began for renovations to the Playground. A Consultant was hired in January 2019 and a new design process for the Playground began. A second Design Review Committee Meeting is scheduled for February 27, 2019.