Upper Green or Paradise Green is a 1.8 acre greensward north of the center of Stratford at the intersection of Main Street and Huntington Road. Large shade trees and evergreens are randomly planted throughout to create a dense canopy of leaves. Near the center is the focal point; a new bandstand (1990), grand in scale and with a Doric colonnade supporting the roof with two diminutive towers. A curving asphalt path flanked by shrubs provides wheelchair access from Main Street and Huntington Road. In the northwest corner is a fan-shaped memorial concrete bandstand. In the opposite corner is a bus shelter and a semi-circular paved area with benches to provide additional seating for those waiting for the bus. The green is flat but uneven and there are bare spots in places. At the southern tip is a proliferation of temporary signs announcing upcoming events.

Primarily modest two-story, late 19th and early 20th century homes of similar scale line Huntington Road and the lower part of Main Street, providing consistent enclosure for the green. Some of these have been converted to commercial use, as has the large, handsome Italianate house at the northwest corner. Near the middle of the block on Huntington Road is the steepled Stratford Baptist Church (1949). The streetscape north of commercial block on Main Street is comprised of small scale commercial establishment that maintain the shallow setback. The exception is the gas station.

The area around the green remained residential with a few houses belonging to the early families ranged around it until 1894 when a trolley line was extended from the New Haven Railroad to Paradise Green. New houses constructed around the green brought residential development to the area. By 1940, the streetscape around the green was built up. Seymour Well's general store, which stood on Main Street opposite the green when the trolley was first in place, was replaced by a solid block of commercial buildings.

The schoolhouse which was replaced by a tennis court at the turn of the century has been replaced by a large oval octagonal gazebo in 1990. It is the product of the Paradise Green Association, who, in conjunction with the Town of Stratford, launched a revitalization plan for the green and streetscape in 1989.