It is served by MBTA bus routes 14, 22, 29, 41, and 44, which operate into an off-street busway located adjacent to the station.

[8][9] Starting in 1891, the Old Colony Railroad (acquired in 1893 by the New York, New Haven and Hartford Railroad) raised the section of its main line through Jamaica Plain (extending from Massachusetts Avenue to Forest Hills) onto a 4-track stone embankment to eliminate dangerous grade crossings.

[1] Although the five NYNH&H stations in Roxbury and Jamaica Plain continued to operate, they were ultimately unable to compete with the Elevated.

The Washington Street Elevated was permanently closed on April 30, 1987, and the new southern half of the Orange Line, including Stony Brook, opened on May 4.

The improvements at the station were designed to reduce criminal activity as well as provide a more welcoming atmosphere for transit riders.

[14] The entire Orange Line, including Jackson Square station, was closed from August 19 to September 18, 2022, during maintenance work.