There is something about exploring a city on foot that changes the way you understand it.

From a car or train window, Toronto can appear to be a city defined by height: soaring office towers, mirrored glass, construction cranes, and a skyline that seems determined to keep growing. At street level, however, the city becomes far more intimate. Old stonework appears beneath the towers. Narrow lanes open unexpectedly between buildings. Carved faces peer down from archways.

That was the Toronto we discovered on the Old Town Free Walking Tour with Toonie Tours.

We joined our knowledgeable guide, Eric, on a cold, grey day. It was the kind of day that makes you pull your coat a little tighter and appreciate every warm lobby and underground passage. Somehow, though, the chilly weather makes a city walking tour feel even cozier. The group gathers closer. Stories become small shelters from the cold. Every indoor stop feels like a reward.

Beginning at Berczy Park, the walk carried us from the playful dog fountain and iconic Gooderham Building into streets where old stone façades stand in the shadows of glass towers. Toronto is constantly building upward, but traces of the earlier city remain tucked between the skyscrapers.

Eric introduced us to the idea of facadism, a preservation technique in which the exterior of a historic building is retained while a modern development rises behind it. Once you know what to look for, you begin seeing it everywhere. Some preserved façades blend almost seamlessly into their new surroundings, while others look like theatrical scenery attached to a much larger building.

As the temperature dropped, we descended into the PATH, Toronto’s vast network of mostly underground pedestrian corridors. The system connects office towers, transit stations, shops, restaurants, and downtown attractions, allowing thousands of people to move through the city while sheltered from winter weather.

Exploring the PATH was one of our favorite parts of the tour. It felt like discovering another Toronto beneath the streets, a polished and warm maze hidden below the Financial District. Following Eric meant we could enjoy its ornate interiors and unexpected passageways without worrying about navigating the notoriously confusing network ourselves.

Back above ground, the tour continued toward one of Toronto’s most imposing landmarks: Old City Hall. Designed by Edward James Lennox and completed in 1899, the Richardsonian Romanesque building is covered with elaborate stonework, including animals, fantastical creatures, plants, and wonderfully expressive human faces.

Then came one of the most memorable stories of the walk.

According to Toronto legend, city officials refused to let Lennox place his name prominently on the completed building as he was over-budget and over-time. Lennox responded by working his name into the exterior stonework. But his revenge may not have ended there. Grotesque and decidedly unflattering faces carved around the entrance are said to represent some of his harshest critics from the city government.

Whether every face can truly be matched to a specific official is difficult to prove, but the story makes the building impossible to view in quite the same way. Suddenly, the carvings feel less like decoration and more like grudges preserved in sandstone.

Across the street, Toronto’s modern City Hall offers a dramatic contrast. Its two curved towers rise around a circular council chamber, creating a bold mid-century landmark beside the heavy stone arches and clock tower of its predecessor. Standing between them feels like standing between two very different versions of Toronto.

Nearby, the curious kissing gates at Osgoode Hall offered another wonderfully peculiar story. The narrow cast-iron passageways may have been intended to keep cattle off the grounds, though theories involving invading soldiers, baby carriages, and overly well-fed lawyers are much more entertaining.

By the end of the walk, Toronto had revealed itself in layers: historic façades beneath glass towers, curious legends behind familiar landmarks, and an entire city still moving beneath the streets.

Toronto may be known for its skyline, but it is the carved faces, hidden passageways, old grudges, and stories beneath the towers that stay with you