Market to Square

Toronto is best understood at street level, on foot and at your own pace, with someone who knows which stories are worth stopping for. This private walking tour moves through two centuries of history, from the oldest corner of the city to its grand civic heart.

It begins at St. Lawrence Market, which has been feeding Toronto since 1803 in a building that once held the council chambers, the police station and the city jail under one roof. From there you walk into Old Town, the original settlement of York, past Berczy Park and its celebrated dog fountain to the Gooderham Flatiron Building, a wedge of red brick squeezed into a narrow corner since 1892, and the story of the whisky family behind it.

The Financial District shifts the register entirely, with Art Deco gems and Victorian survivors beneath the towers of Bay Street, hidden corners and the PATH, and the Beaux-Arts grandeur of Union Station's Great Hall. The walk closes at Nathan Phillips Square, framed by Viljo Revell's curved City Hall and the Toronto Sign, with Old City Hall and its gargoyles keeping watch alongside.