Toronto Walking Tour: Old Town York to the Distillery District

Long before Toronto had a skyline, it was the Town of York, a muddy grid of a few blocks by the lake, and the oldest part of the city still sits just east of the bank towers, in streets of red brick, church spires and a market that has been trading since the early 1800s. This walk heads east through that old town and the Irish working neighborhood of Corktown into the cobbled lanes of a Victorian whisky distillery, and ends in a new park on a grassy hill with the whole skyline spread out behind you. It starts at St. James Cathedral on King Street and runs about three kilometers, flat all the way, a gentle half day among the best self-guided walking tours in Canada for anyone who likes their history with a good lunch in the middle.

Before you set off

The walking takes about three quarters of an hour, but give it two and a half to three hours so you can browse the market, step into the first post office and wander the Distillery's lanes properly. The whole route is flat and paved, with some uneven cobbles in the Distillery, so any comfortable shoes will do. The market is liveliest in the morning and keeps its own weekly schedule, closing on some days, so check before you go; the same goes for the post office museum, which has short hours. Toronto summers are warm and humid and winters are properly cold, with a sharp wind, so dress for the season. The Distillery is busiest on weekends and in the weeks before Christmas, when its winter market fills the lanes, and it is quieter and easier to photograph on a weekday morning. Corktown Common at the end has open lawns and little shade, so bring a hat on a hot day. Streetcars run along King Street if you want a lift back to downtown afterward.

St. James Cathedral

Stand on the corner of King and Church streets and look up, and keep looking up. The spire of St. James Cathedral climbs more than ninety meters above you, the tallest church spire in Canada, finished in 1874. This was the parish church of the Town of York from its earliest years; the congregation goes back to the late 1790s, and its first church on this spot was a small wooden building. The present cathedral, in pale brick and stone with tall pointed windows, was built after the Great Fire of 1849 tore through this part of the city and destroyed the church before it. It was designed by Frederick Cumberland, one of the busiest architects of Victorian Toronto. King Street, in front of you, was the main street of the young town, lined with its best shops and finest houses. Just east of the cathedral lies St. James Park, with a formal Victorian-style garden of clipped hedges and flower beds and a little gazebo, a lovely place to sit for a minute if you arrived early. If the doors are open, step inside to see the stained glass and the calm, high interior. From here, walk south on Church Street, away from the spire, for two short blocks. In about three minutes the street opens up where several roads meet, and a narrow red-brick building points straight at you.

Gooderham Building and Berczy Park

Stand at the point of the triangle and look at the narrow brick building in front of you. This is the Gooderham Building, Toronto's Flatiron, squeezed onto a wedge-shaped lot where Wellington and Front streets come together. It went up in 1892, about a decade before New York's more famous flatiron, as the office of George Gooderham, head of the distilling firm whose old works you will reach later on this walk. Look at the rounded tip with its turret and copper roof, and then walk around to the back, where the flat rear wall is covered in a large mural that plays tricks with the eye. Behind it, in the little triangle of land, is Berczy Park, named for William Berczy, an early settler, painter and builder who helped lay out roads for the young colony. The park was redesigned a few years ago around a fountain that makes everyone smile: more than two dozen cast-iron dogs of every breed sit on its tiers, spouting water and gazing up at a giant golden bone at the very top. Look closely and you will find a cat among them too. With the Flatiron in front, the glass towers of the Financial District behind it and the dogs at your feet, this is one of the most photographed corners of the city. To move on, walk east along Front Street, about three minutes, to the long brick front of the market hall.

St. Lawrence Market

You are standing at the St. Lawrence Market, and people have been buying and selling food on this spot since 1803. Before you go in, look at the middle of the long brick front facing Front Street. The core of this building was once Toronto's city hall, built in the 1840s, and the city council met upstairs in a chamber that still exists, now used as a gallery space when it is open. When the council moved to a grander home in the 1890s, the building was taken over by the market, and the great hall behind the old facade was built around it, with its wide arched roof of steel and glass. Step inside and let your nose take over. There are counters of cheese, fish and smoked meat, bakeries, spice stalls and produce stands on the main floor and on the lower level. Toronto was once a major meatpacking town, which earned it the nickname Hogtown, and the classic thing to eat here is a peameal bacon sandwich, thick slices of cornmeal-rolled back bacon in a soft bun. This is the best lunch stop on the walk, so do not rush. When you are ready, leave the market and walk north on Jarvis Street, the street along the market's east side. Cross King Street and turn right onto Adelaide Street East. In about five minutes you will reach a small brick building with tall windows on Adelaide Street.