By November 1864 he was touring with the "Australian Troupe" variety artistes, demonstrating speed walking.

[2] Such races were popular subjects for gambling, and he was nine years old, 3 feet 10 inches (117 cm) high, and weighed 54 pounds (24 kg),[3] In 1867, he completed 300 laps of a circuit created in the Royal Victoria Theatre, Sydney, a total of 5 miles (8.0 km), in under 50 minutes[4] It is not known whether this exhibition was provided for gambling purposes, but it was said that his backers[who?]

[5] Another challenge, to walk seven miles within the hour, was staged at the track attached to Goyder's Red House hotel in Northcote.

It started at £30 to £10, and Day was loudly supported each time he passed the judge's stand, but when it was clear he had no prospect of succeeding, one sympathizer invaded the track and carried him away.

Dubbed the "Wonder Walker",[7] he rode Nimblefoot to victory in the Hotham Handicap of 5 November 1870[8] and the same combination was judged winner of the 1870 Melbourne Cup in a very close finish, ahead of Lapdog,[9] a record[10] which held until 1876.