Wooster Square is located east of the city center in a residential neighborhood in New Haven. It is bounded by Greene Street on the north, Wooster Street on the east, Chapel Street on the south and Academy Street on the west. All are narrow one-way streets with traffic moving in counter-clockwise direction around it with the exception of Chapel Street, a two-way street.

The square is a rectangular-shaped open space about twice as long as it is wide and slopes upwards slightly at the edges to meet the sidewalk which surrounds it. Several elements of the landscaping can be traced to the New Haven Green including the fence and the paths. The fence just inside the sidewalk has cast iron rails between sandstone posts. Some of the more deteriorated ones have been replaced by granite ones. The asphalt radiate from the center to the corners and the midpoints of each side. Three other paths cross it diagonally to form almost a cobweb of paths. Flowering shade trees are planted at even intervals around the perimeter. The interior is shaded by many trees, primarily maple and oak, many of them mature. Although they appear to be randomly planted, there is evidence of the trees once having been planted in rows, particularly along the long sides of the square and the paths.

Near the southwest corner is a bronze statue of Columbus on a sandstone and granite base, dedicated in 1892, celebrating the 400th anniversary of the discovery of the Americas. Near the southeast corner is a pink World War II memorial and in the northeast corner is a small boulder with a bronze plaque memorializing Columbus School students who died in the same war.

Parallel parking is allowed around the perimeter on all the streets and provides almost as much enclosure for the green as the tight frame of buildings around it. Most of them are substantial, single-family, frame houses or masonry apartment buildings constructed in the Italianate style. A row of three and four story Italianate sandstone apartment houses (six buildings) along Chapel Street lend a particularly urban atmosphere to the square. Two Catholic churches face it, on Wooster and Chapel Streets. Recent incursions have occurred in the form of two long, concrete, two-story buildings, one along Wooster Street and one along Chapel. While their massing and form is out of character with the other buildings, they maintain the street wall, thereby providing consistent enclosure for the picturesque 19th century urban space.