Front Street, Toronto
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When John Graves Simcoe, the first Lieutenant Governor of Upper Canada, laid out the town plan for his new capital, York, Upper Canada, Front Street was the most southerly street, paralleling the bluffs that formed the shoreline.
The capital grew and expanded, being renamed Toronto, Ontario, in 1834, and Front Street was extended several kilometers west. As the city expanded the shoreline was extended several hundred meters south, with landfill, so Front Street no longer fronted the shoreline.
Prominent buildings were built on Front Street, including Union Station, the St Lawrence Market, the CN Tower and the Skydome.