The Paddlewheeler City of Toronto
The City of Toronto was built in 1864 and travelled between Toronto and Niagara-on-the-Lake, which is featured in the background of the painting. It was painted for the ship's owner, Captain Duncan Milloy (1825–1871), who lived in Niagara-on-the-Lake on a property now known as the Oban Inn. W. E. Wright lived nearby. Following a competition in 1867, the City of Toronto was proclaimed "the fastest on the lake" by a local newspaper, the St. Catharines Constitutional. When purchased, the painting was accompanied by an engraved goblet and Milloy's navigation guidebook.