East of the downtown towers lies Old Town Toronto, the patch of streets where the town of York was laid out in the 1790s. This guide covers seven places there, from a fountain full of cast-iron dogs to a Victorian whisky distillery, all within an easy walk of each other and none of them on our scavenger hunt route, so they make a good second half to a day in the city.
Berczy Park and the dog fountain
Berczy Park is the small triangle of green between Front Street and Wellington Street, named after William Berczy, the architect and surveyor who worked with Upper Canada's first governor, John Graves Simcoe, on founding York. The Montreal landscape architect Claude Cormier redesigned it, and it reopened in 2017 with a fountain that quickly became one of the most photographed spots in the city.
- The fountain has two tiers and 27 cast-iron dogs, each spouting water, all looking up at a golden bone on the top. Hidden among them is a single cat, nicknamed Pam McCat after the city councillor Pam McConnell, who championed the park.
- At ground level there is a trough where real dogs can drink, and a second cat sits on an electrical box at the park's south-west corner.
Gooderham (Flatiron) Building
At the eastern tip of Berczy Park, where Front and Wellington meet at a sharp angle, stands the Gooderham Building. This red-brick wedge was completed in 1892 to designs by David Roberts Jr. for the distiller George Gooderham, and it served as the head office of the Gooderham and Worts distillery until 1952. It is ten years older than the famous Flatiron Building in New York.
- Walk around to the back: the flat western wall carries a large trompe-l'oeil mural by the Canadian artist Derek Besant, best seen from Berczy Park.
- Look up at the rounded tower at the narrow end, with its copper-covered roof, and at the way the five floors taper to the point.
St. James Cathedral
A few minutes' walk north on Church Street brings you to the Anglican Cathedral Church of St. James. Its congregation, founded in 1797, is the oldest in the city. The present Gothic Revival church, designed by Frederick Cumberland and Thomas Ridout, opened in 1853 after the previous one burned in the great fire of 1849. Henry Langley finished the tower and spire in 1874, and at 92.9 metres it was for about 25 years the tallest structure in Canada. It is still the tallest church spire in the country.
- Listen for the bells: in 1997 the tower received a ring of 12 change-ringing bells, one of only two such 12-bell peals in North America.
- The chiming clock on the tower was installed about a year after the spire was finished, and St. James Park and its garden lie right next to the church.
Toronto's First Post Office
Head east along Adelaide Street to number 260, a modest brick building that is easy to walk past. It was built in 1832 and opened as a post office in 1833, when Toronto was still called York. It is the oldest purpose-built post office in Canada that worked as part of the British Royal Mail, and the only one of its kind still standing. Today it is both a small museum, run by the Town of York Historical Society, and a working post office, so you can still send a letter from here.
St. Lawrence Hall
Back down at the corner of King and Jarvis streets, St. Lawrence Hall was built in 1850 and 1851 as Toronto's public meeting hall, to designs by William Thomas. It is a Renaissance Revival building with a cupola on top and a large ballroom upstairs, and for decades it was where the city went for concerts, lectures, balls and political meetings. John A. Macdonald and George Brown, both Fathers of Confederation, spoke here.
In September 1851 the hall hosted the North American Convention of Colored Freemen, a three-day gathering of abolitionists that condemned the American Fugitive Slave Act. The building was fully restored in 1967 as a centennial project and became a National Historic Site that year. Much later it hosted the first two Juno Awards, Canada's music prizes, in 1970 and 1971.
St. Lawrence Market
Just south, across Front Street, is St. Lawrence Market. A market has been held on this site since 1803. The South Market building, the one with the long arched hall, still contains part of the building that served as Toronto's City Hall from 1845 to 1899. In 2012, National Geographic named St. Lawrence Market the world's best food market.
- Go upstairs at the front of the South Market to the Market Gallery, which fills the old city council chamber and shows exhibitions about Toronto's history.
- Try a peameal bacon sandwich, the city's signature snack. Carousel Bakery in the South Market is the stall most associated with it; its owners were given the key to the city in 2025.
- Across the street, the new North Market building opened in 2025 and is home to the traditional Saturday farmers' market.
The Distillery District
Finish further east at the Distillery District, the former Gooderham and Worts distillery, founded in 1832 by the same family that built the Flatiron. At its peak it produced more than two million gallons of whisky a year, much of it for export. Production ended in 1990, and in 2003 the site reopened as a pedestrian-only quarter of shops, galleries, cafés and restaurants. It is a National Historic Site and is often described as the largest collection of Victorian industrial architecture in North America.
- Wander the brick-paved lanes between more than 40 heritage buildings, and look out for the large contemporary sculptures placed along them.
- If the lanes look familiar, that's because more than 800 film and TV productions have been shot here since 1990. In late autumn and winter a Christmas market, now called the Distillery Winter Village, fills the streets.
How to see them in one walk
Start at Berczy Park, a few minutes' walk east of Union Station and the Hockey Hall of Fame, and see the Gooderham Building from the park. Walk north up Church Street to St. James Cathedral, then east along Adelaide Street to Toronto's First Post Office. Turn south to St. Lawrence Hall at King and Jarvis, cross to St. Lawrence Market for lunch, and continue east along Front Street and Mill Street to end the day in the Distillery District.
See Toronto with World City Trail
Our Toronto scavenger hunt turns the city centre into a game you play on your phone. The route links 10 other landmarks, including Union Station, Old City Hall, Nathan Phillips Square and the CN Tower, so the places in this guide are a good addition before or after the game.
If you prefer a different format, there is also a self-guided walking tour and an outdoor escape game in Toronto.
Play the Toronto scavenger hunt →
Take the self-guided walking tour of Toronto →
Play the outdoor escape game in Toronto →
Facts checked in November 2026.