The ten blocks that were the whole of York in 1793, with a Victorian assembly hall where Jenny Lind sang and abolitionists met.
When John Graves Simcoe laid out York in 1793, the town was ten blocks between what are now George and Berkeley Streets, south of Adelaide. Everything else was forest.
That grid is still there, and the area is now marketed as Old Town — though it was called the St Lawrence Ward for most of its life.
St Lawrence Hall
Built in 1850 after a fire destroyed the previous market building, in Renaissance Revival with a cupola and a clock, and for thirty years it was Toronto’s principal public room.
Jenny Lind sang here in 1851 on her North American tour. George Brown, a Father of Confederation, spoke here. Frederick Douglass addressed an audience here, and the Anti-Slavery Society of Canada held meetings in the hall — Toronto being a terminus of the Underground Railroad, with a Black community established from the 1830s.
It was nearly demolished in the 1960s and was restored for the 1967 centennial. The Great Hall upstairs is used for events and can usually be looked into.
St James Cathedral
The Anglican cathedral, 1853, with the tallest spire in Canada at 93 metres and the tallest in North America when it was built. Free to enter, and the churchyard is a small park.
The congregation dates from 1797 and the earlier buildings on the site burned down twice.
The Gooderham Building
At Front and Wellington, the flatiron of 1892 built for the distillery family — five storeys of red brick narrowing to a rounded point, with a trompe-l’oeil mural on the back wall.
It predates New York’s Flatiron by ten years and it is the single most photographed building in Toronto. Stand on the east side of Front Street at dusk with the bank towers behind it.
The rest
St Lawrence Market — see its own entry — occupies the 1845 south building, which incorporates the old City Hall.
The First Post Office, from 1833, on Adelaide Street East, still operating as a post office and museum, where you can write with a quill and have it sealed with wax.
Berczy Park, with the dog fountain — 27 cast-iron dogs and one cat, all looking up at a bone. It is ridiculous and Toronto loves it.
Practicalities
All free except the First Post Office museum, which is by donation.
King station on Line 1, or streetcars along King and Queen. Everything above is within a fifteen-minute walk of everything else.
More History
The Distillery District
Forty-odd Victorian industrial buildings from what was once the largest distillery in the world, pedestrianised and full of galleries.
Evergreen Brick Works
A brickworks that supplied half of Victorian Toronto, abandoned, flooded, and turned into a park with a farmers' market in the kilns.