The first Madison Square Garden, ca. 1891.

Originally a station for the Cornelius Vanderbilt-owned New York & Harlem Rail Road, P.T. Barnum converted the terminal space into the Great Roman Hippodrome Arena in 1871. It became Gilmore's Garden, named for the entertainment impersario Patrick Gilmore, in 1876. The following year, the area hosted the first edition of the competition that would become the Westminster Kennel Club Dog Show.

Following Vanderbilt's death, William Kissam Vanderbilt assumed control of the site, changing the name to Madison Square Garden. In 1889, the younger Vanderbilt sold the aging venue to a group of Gilded Age industrialists who hired architect Stanford White to design a new Garden on the same site.