Bennett Field is located behind the state Veterans Memorial Pool, off from Main Street in Webster Square.

Bennett Field was purchased in 1943 from Worcester Street Railway and additional property was added from tax title land, making the park a total of 6.67 acres. The old trolley station foundation is still underneath the field.

According to the site’s most recent master plan, the retaining wall at the park along Gates Lane is being restored, the ball field is being rebuilt, a new basketball court is being built and an environmental trail is being implemented. The playground has been completely redesigned, as has the parking lot.