In 1853 he first travelled to East Maitland, New South Wales as a livestock agent. He returned to Leeds two years later on the ship "Speedy", when he sold his business. He thereafter diversified his business and political interests and returned to colony. On 13 December 1861, he and James Brunker purchased 600 head of cattle at a sale in the Northumberland Hotel, Maitland. In March 1862 a new municipality of East Maitland was created and elections were called. Stephen Scholey was elected Alderman for the new municipality on 25 April 1862; and on 2 May 1867, he was commissioned by the Colonial Office, with a Letters Patent from the colony's governor, Sir John Young (and witnessed by Henry Parkes, who had stood for election to the Legislative Assembly in Scholey's East Maitland in August 1863, but was defeated by J. B. Darvall), to that effect, to be Warden and President of the Maitland District Council.