After a provincial racing charter was granted in 1894 to the York Riding and Driving Association to operate horse racing and sell liquor, a half-mile track was laid out on 25 acres (10 ha) of land on the west side of Dufferin Street owned by Charles Leslie Denison.

[4] Orpen appealed to Canadian Prime Minister Wilfrid Laurier directly and was granted a federal charter.

[10] During World War II, Long Branch was closed and some of its stakes races were held at Dufferin Park.

[12] Taylor paid a reported CA$4 million for Orpen's tracks and racing charters and transferred them to the Ontario Jockey Club on December 1, 1955.

He built an estate on 400 acres (160 ha) of land near Alton, which he sold in 1972 to develop a housing sub-division.

It was used by local high school Central Commerce Collegiate for athletics meets.

[15] From 1951, the site was also used for a musical theatre production in a tent, called Melody Fair.