The Jackson Avenue station opened on November 26, 1904, as part of the initial segment of the IRT White Plains Road Line.

Contract 1 called for the construction of a line from City Hall north to Kingsbridge and a branch under Lenox Avenue and to Bronx Park.

[5] The initial segment of the IRT White Plains Road Line opened on November 26, 1904, between East 180th Street and this station.

[6][7][8] Elevated service via this connection was resumed on October 1, 1907, when Second Avenue local trains were extended to Freeman Street during rush hours.

[7] To address overcrowding, in 1909, the New York Public Service Commission proposed lengthening the platforms at stations along the original IRT subway.

[9]: 168  As part of a modification to the IRT's construction contracts made on January 18, 1910, the company was to lengthen station platforms to accommodate ten-car express and six-car local trains.

[7] The New York State Transit Commission announced plans to extend the southbound platforms at seven stations on the line from Jackson Avenue to 177th Street to accommodate ten-car trains for $81,900 on August 8, 1934.

In 1977, the New York City Transit Authority (NYCTA) decided that it was not justified to fund the rebuild of the token booth and the cost of manning it due to the low number of entries at the platform.

[20] West of this station, the elevated structure widens with room for two more tracks, where the connection to the Third Avenue Line was located.

They depict images from six Latin American stories, including How Fire Came to the Rain Forest and The King That Tried to Touch the Moon from the Lesser Antilles.

[17]: 5–6 On the Manhattan-bound side, doors from the platform lead to a small waiting area, where a turnstile bank provides entrance/exit from the station.

[17]: 6  Outside of fare control, there is a token booth and two sets of doors leading to two staircases facing in opposite directions that go down to the west side of Westchester Avenue.

[17]: 5  Outside fare control, a set of doors lead to balcony where two double-flight, twisting staircases go down to the northeast corner of Westchester and Jackson Avenues.