The community was linked in 1849 to the City of Toronto by H.R. Williams' horse-drawn omnibus service.  In 1853 it was incorporated as the Village of Yorkville.  Despite annexation by the City of Toronto in 1883, Yorkville remained a quiet community of predominantly middle- and working-class people well into the 20th-century.

In the 1950s, artists and actors transformed the area into a thriving arts community.  By the mid- to late 1960s, Yorkville had become famous for its 'hippies", folk music and coffee houses.  Redevelopment has since  altered much of the old incorporated Village.  Still, streets north of Yorkville Avenue, west of Avenue Road (now part of the Annex), and east of Yonge Street (now part of South Rosedale) retain much of their 19th- and 20th- century character.

In its second floor Council Chamber, local politicians debated, amongst other things, "the running at large of Pigs and Swine and Poultry", the planking of sidewalks and the "prevention of immoderate driving".  In 1861, the privately owned horse-drawn Toronto Street Railway commened service from the Town Hall to the St. Lawrence Market.  After the clock tower was completed in 1889, the Town Hall's bells sounded the working day and rang for fire alarms.

After annexation in 1883 ended Yorkville's village government, the Council Chamber was used as a public library.  The building also housed the Yorkville Company of the York Rangers, the Naval Club, and the offices of the Toronto Street Railway, and had space for community use.

The Yorkville Town Hall was destroyed by fire on November 12, 1941.  All that remains is the carved stone coat-of-arms, since mounted on the Yorkville Fire Hall.