It runs for approximately 4.9 kilometres (3.0 mi) from a junction with Rolleston Avenue at its western end, directly opposite Christ's College, to the suburbs of Linwood and Avonside in the east.

For the majority of its length it runs due west-east, with the section from the central city's eastern edge to Linwood veering to the northeast.

As it crosses Linwood Avenue, the street turns northeast and narrows, becoming a suburban arterial road.

A bridge, Dallington Bridge, crosses the river at this point, and the street continues as Gayhurst Road through a former residential area which was razed as a result of the 2011 Christchurch earthquake.

Major sites on or adjacent to Gloucester Street include Rolleston House, a NZHPT Category II-listed historic place;[1] Gloucester Street Bridge, a NZHPT Category II-listed historic place;[2] Christchurch Art Gallery, at the corner of Montreal Street, and the neighbouring Centre of Contemporary Art; the Isaac Theatre Royal, a NZHPT Category I-listed historic place;[3] Te Pae Christchurch Convention Centre, between Oxford Terrace and Colombo Street; Latimer Square; and Christchurch East School.