Toronto History Walks: A Self-Guided Route Through Old Town

Of all the Toronto history walks you can do, the best one is free, self-guided and already mapped by the City. It runs through Old Town, from St. Lawrence Market east to the Distillery District, and it covers the ground where the Town of York became the City of Toronto. Thirteen numbered stops, one afternoon, no ticket.

The City of Toronto publishes the route as a downloadable map called From Town to City and Beyond. We walked the order below off that map, checked every building against its own official source in November 2026, and found two things on the City’s version that are now out of date. Those corrections are in here.

Toronto history walks: the route in one list

Stop	Where	Built
South St. Lawrence Market and City Hall	95 Front St. East	1845 and 1902
North Market, on the 1803 market block	92 Front St. East	Rebuilt, opened 2025
Gooderham “Flat Iron” Building	49 Wellington St. East	1892
King Edward Hotel	37 King St. East	1903
Courthouse Square	Court Street	1800
St. James Cathedral	65 Church St.	1853
St. Lawrence Hall	157 King St. East	1850
Bank of Upper Canada	252 Adelaide St. East	1827
Toronto’s First Post Office	260 Adelaide St. East	1833
Young People’s Theatre	165 Front St. East	1883
First Parliament site	Berkeley St. at Front	1799
Little Trinity Church	425 King St. East	1842
Enoch Turner Schoolhouse	106 Trinity St.	1848
Gooderham and Worts Distillery	55 Mill St.	1832 onward

Start at the market, where the city started

The front of St. Lawrence Market at 95 Front St. East dates to 1845, and it was built as Toronto’s first official City Hall. The police station, holding cell, market and council chamber were all in the one building. Council moved out in 1899. Go up to the second floor and you are standing in the former council chamber, which is now the Market Gallery, a City of Toronto museum. General admission is free, and it is open Wednesday to Sunday, 11 a.m. to 4 p.m., closed statutory holidays.

The South Market itself runs Tuesday to Friday 9 a.m. to 7 p.m., Saturday 7 a.m. to 5 p.m., Sunday 10 a.m. to 5 p.m., and is closed Mondays. Our St. Lawrence Market guide has the stalls worth your time.

Cross to 92 Front St. East. Lieutenant Governor Peter Hunter declared this the official market block in 1803, and market buildings have stood here since 1820. This is the City’s first out-of-date stop. Its map still says a new four-storey North Market is “scheduled to open in 2016.” It is built and open: the Saturday Farmers’ Market returned to the new St. Lawrence Market North building on April 5, 2025, with a community grand opening that May. The Saturday market runs 5 a.m. to 3 p.m.

The loop up to King and Adelaide

Walk west to Wellington and Front, where the Gooderham “Flat Iron” Building of 1892 wedges into the intersection. David Roberts Jr. designed it as the head office of the Gooderham financial empire, and that empire was built on liquor sales. Remember that, because the walk ends at the distillery that paid for it.

Up at 37 King St. East, the King Edward Hotel opened in 1903. E.J. Lennox designed it, the same architect as Casa Loma and Old City Hall, and George Gooderham paid for it to stop the city’s business drifting west of Yonge. Before the hotel, this was the site of York’s first jail, built in 1799.

North on Toronto Street to Court Street. The gallows, known as Hangman’s Square, stood here behind the courthouse from 1800. Public hangings drew crowds, and parents brought children to watch as a deterrent. Samuel Lount and Peter Matthews were hanged on this spot for their part in the 1837 Rebellion. It is an ordinary laneway now with no marker that announces any of this, which is exactly the kind of thing we dig into on Case Theory.

St. James Cathedral at 65 Church St. is the fourth church on the site. The congregation goes back to 1793 and the first Anglican service in the Town of York. Fires took the building in 1839 and again in 1849, and the current Gothic Revival cathedral opened for services in 1853. The spire went up in the 1870s and the City’s tour calls it the tallest in Canada. The cathedral is open to visitors Monday to Saturday, 10 a.m. to 3 p.m., and Sundays for services.

St. Lawrence Hall at 157 King St. East went up in 1850, designed by William Thomas after the great fire of 1849 levelled this stretch of King Street East. It became the social centre of the city, and the part worth standing still for: the Anti Slavery Society met in the hall, and in September 1851 members of the Black community from Toronto and across the province organized the Convention of Coloured People here. The ground floor is a working event venue, so you may only see the outside.

East on Adelaide, 252 Adelaide St. East was the first permanent home of the Bank of Upper Canada, chartered in 1821. Next door at 260, Toronto’s First Post Office was built in 1833 for postmaster James Scott Howard and still works as a Canada Post dealer and a museum. The Town of York Historical Society runs it, it is open seven days a week, and admission is by donation. You can write a letter with a quill and have it sealed with wax.

Down to the water, and the Distillery

Back on Front Street East, 165 Front St. East is now Young People’s Theatre. This is the City’s second out-of-date stop: the map still calls it the Lorraine Kimsa Theatre for Young People, a name the company no longer uses. The building was put up in 1883 as a stable for the horses that pulled the Toronto Railway Company’s streetcars. When those horses were retired for electric power in 1891 it became a generating plant, which ran until 1906, when the company started buying power from Niagara Falls. The TTC used it as a warehouse, it sat empty and marked for demolition, and YPT opened its first show inside on December 22, 1977.

At Berkeley Street between Front and The Esplanade is the First Parliament site. York was named capital of Upper Canada in 1793, and the Parliament Buildings here held the government, the courthouse and the Anglican church. American troops burned them in 1813 during the War of 1812. They were rebuilt in 1815 and burned down again in 1826. Set your expectations before you arrive: the City says plainly that the site has no visible historic artifacts, and the archaeology sits underground in contaminated soil. You are looking at a lot and some panels.

Two short detours before the finish. Little Trinity Church at 425 King St. East dates to 1842 and is the oldest surviving church building in the city. Bishop John Strachan founded it for the working class east end, and the money came in part from distillery owners William Gooderham and James Worts. Behind it at 106 Trinity Street, the Enoch Turner Schoolhouse was built in 1848 by a brewer who paid for it himself because the city council refused to open free schools. The Ontario Heritage Trust plaque calls it “the oldest remaining in Toronto,” and it opened with space for 240 pupils.

Finish at 55 Mill St., the Distillery District. Gooderham and Worts was established in 1832, two years before York became Toronto, and grew into the largest distillery in the British Empire. Mill Street is named for the windmill that powered a grist mill here before the liquor business. The site is open 364 days a year: Monday to Wednesday 10 a.m. to 8 p.m., Thursday to Saturday 10 a.m. to 9 p.m., Sunday 11 a.m. to 8 p.m. Our Distillery District guide covers what to eat there.

One timing warning for right now. The Distillery Winter Village runs November 12, 2026 to January 3, 2027, and on Friday, Saturday and Sunday from 4 p.m. you need a ticket to get in, starting at $16 plus HST and service charge. Before 4 p.m. is free every day. Finish your walk in the afternoon and you walk straight in. Full detail is in our Toronto Christmas market guide.

How to walk it well

Pick Saturday or skip Monday. Monday closes the South Market and the Market Gallery, which takes the best indoor stop off the list.
Go east, not west. Walking toward the Distillery means you finish somewhere with food and heat, which matters in November.
Free museums along the way. General admission to all ten City-run Toronto History Museums is free. Mackenzie House at 82 Bond St. is a ten minute walk north of St. James and opens Wednesday to Sunday, 11 a.m. to 4 p.m.
Transit, not parking. King station or Union puts you at the start. Our TTC guide covers fares.
Two of these stops are haunted, depending who you ask. Our Toronto haunted places guide has the real history behind the stories, and Toronto hidden gems has more places like these.

Hours, dates and prices were checked in November 2026. Confirm on the official site before you cross the city for one building.

Quick answers

Is there a free self-guided history walk in Toronto?

Yes. The City of Toronto publishes a free self-guided historical walking tour of the St. Lawrence Neighbourhood called From Town to City and Beyond, with 13 numbered stops between Yonge Street and Mill Street. You can download the route map from toronto.ca and walk it any day, at no cost.

How long does the Old Town Toronto history walk take?

Allow two to three hours if you stop and read at each building, longer if you go into the Market Gallery or the First Post Office. The whole route sits between Yonge Street and Parliament Street, so nothing is far apart. You can shorten it by skipping the loop up to Adelaide Street.

What is the oldest building on a Toronto history walk?

On this route, the Bank of Upper Canada at 252 Adelaide St. East dates to 1827 and Toronto's First Post Office next door to 1833. Nearby, the Enoch Turner Schoolhouse at 106 Trinity Street is the oldest school building still standing in Toronto, built in 1848.

Can you walk from St. Lawrence Market to the Distillery District?

Yes, and it is the natural second half of this walk. Head east along Front Street East to Berkeley Street, then continue to Mill Street. The Distillery District sits at 55 Mill St. and is open 364 days a year.

Do you need to book a Toronto history walking tour?

Not for this one. It is self-guided and free. The only stops with fixed hours are the Market Gallery and Mackenzie House, both open Wednesday to Sunday, 11 a.m. to 4 p.m., and the First Post Office, which is open seven days a week by donation.

What is the best day to do this walk?

Saturday. The South Market runs 7 a.m. to 5 p.m. and the Saturday Farmers' Market in the new North Market building starts at 5 a.m. Avoid Monday, when the South Market and the Market Gallery are both closed.

Sources

Prices, hours and schedules change. Check the official site before you go. Spot something out of date? Email info@truecitytourism.com. Some links may be affiliate links. Disclosure.