5. Yonge-Dundas Square - 1 Dundas Street East

Yonge Dundas Square is the commercial heart of Toronto, sometimes unfairly called “Toronto trying to be Times Square,” Many big cities have a square or intersection where the neon and giant video billboards seem to be feral, as they do here. In the 1990s there was a desire to create a new, large public space in downtown Toronto as Nathan Phillips Square at City Hall was the only real open space. The design competition was won by Brown + Story Architects, the commercial buildings here previously were razed and the square officially opened in 2002.

Look up on the east side of the square to see the Sam the Record Man neon sign atop the Toronto Public Health building, moved here after the famous record store closed on Yonge Street a few blocks north.

The square’s creation opened up a new, expansive view of the Eaton Centre, Toronto’s downtown mall and office complex that opened in 1977. Created on land owned by the now-defunct Eaton’s department store chain, the complex was designed by German-Canadian architect Eberhard Zeidler and modelled after the Galleria Vittorio Emanuele II in Milan, Italy. The design was ultimately required to respect the Church of the Holy Trinity on the west side of the building as well as Old City Hall. Today it’s one of the, if not the, most visited attractions in Toronto.