The green on Academy Hill is a 4.69 acre open space in Stratford's town center. The el-shaped green is located behind (east of) St. James Catholic Church and Christ Episcopal Church which fronts busy Main Street, buffering the green from the noise of the traffic. The green is bordered by Broad Street on the north, Elm Street on the east and Academy Hill on the south.

Its most dominant feature is the undulating terrain that rolls to the north and the west from its highest point not too far from the southeast corner. Mature trees, many of them maple, provide shade. They are planted primarily along Elm Street and Academy Hill in a random pattern, allowing for vistas to and from the interior of the green. To the west along Broad Street adjacent to the green is a picturesque burying ground with a few scattered trees, including a scion of the Charter Oak, surrounded by a five foot metal picket fence, given by Columbia University in memory of its first president, William Samuel Johnson, buried within.

On the highest point is a Civil War monument, a Union soldier on top a tall base holding a flag. It is made of zinc by the Monumental Bronze Company in Bridgeport, and was dedicated in 1889. The modern war memorials, tall grey granite shafts of various shapes are arranged in a semi-circle facing the Soldiers and Sailors Monument. One commemorates those who served in Korea, one remembers those who served in Vietnam, and the other honors disabled American veterans. Near the Vietnam memorial is a flagpole and a small boulder with a bronze plaque remembering Captain John Carpenter from Stratford who commanded the Jamaica Husiliers in the defense of Fort James when the Dutch fleet of William of Orange recaptured New York from the English. Also on the green are three memorial trees, planted to remember Theodore Roosevelt on his 100th birthday, and Edith Hastings (planted by the League of Women Voters).

On the streets bordering the green are well-preserved 18th and 19th century houses, evenly spaced apart and of similar scale although representing several architectural periods. Of particular note is the Captain David Judson House (about 1750) Academy Hill (street) across from the lower part of the green. Despite its location in the town center close to Main Street, the undulating green hills surrounded by a well preserved historic neighborhood relay a feeling of calm and repose.