Toronto sits on land continuously occupied for 11,000 years, burned by American troops in 1813 and rebuilt as Upper Canada's capital. Its history hides in plain sight: 1815 barracks under a highway, a bank vault beneath Bay Street, and immigrant streets still changing hands.
Toronto's founding site, built 1793 and rebuilt after the American invasion of April 1813. Eight original 1813–1815 buildings survive — Canada's largest collection of War of 1812 structures. Open daily 10:00–17:00; guided tours and musket demonstrations in summer.
Five gaunt bronze figures by Rowan Gillespie mark where 38,560 Irish famine refugees landed in summer 1847 — more than Toronto's entire population of 20,000. A limestone wall lists 675 who died of typhus in fever sheds that season.
Sir Henry Pellatt's 98-room Gothic Revival castle, built 1911–1914 for CAD $3.5 million by architect E.J. Lennox. Pellatt lost it to tax arrears in 1924 after his hydro monopoly collapsed. The 244m tunnel to the stables and Norman Tower are the highlights.
Next door to Casa Loma, the Austin family's 1866 house is restored to the 1920s down to the wallpaper and the electric annunciator bells. Six acres of Victorian and Edwardian gardens sit on the Iroquois shoreline escarpment.
Richardsonian Romanesque pile of pink Credit Valley sandstone, opened 1893. Free 30–45 minute tours cover the 1909 fire that gutted the west wing, the chamber's mahogany, and the mace the Americans stole in 1813 and returned in 1934.
E.J. Lennox's 1899 Romanesque courthouse and city hall, its clock tower the tallest building in Toronto until 1929. Lennox carved caricatures of the councillors who disputed his fee into the arch corbels, and his name into the eaves.
An 1833 post office at 260 Adelaide St E, still operating as a Canada Post branch and a museum. Write a letter with a quill and iron-gall ink, seal it with wax, and have it postmarked with the 1830s hand stamp.
Toronto's oldest continuously operating tavern, licensed 1849 at King and Bathurst, when it stood at the city's western edge beside the Fort York garrison. The frame building survived the 1904 Great Fire that levelled 100 buildings to the east.
Little Trinity (1843) is Toronto's oldest surviving church building, founded for Irish labourers barred by pew rents at St James. Behind it, brewer Enoch Turner's 1848 schoolhouse was the city's first free school, built during a cholera epidemic.
A Jewish market from the 1920s, when 60,000 Eastern European Jews filled the narrow Victorian streets and sold from front-yard stalls. Successive Portuguese, Caribbean, Chinese and Latin American waves layered on top; the shopfronts still show it.
The 1929 John Street Roundhouse, 32 bays around a working turntable, where CPR serviced steam locomotives until 1986. Restored steam engine 6213, a 1929 Cabin D interlocking tower, and the story of the rail lines that made Toronto.
At Front and Parliament, an archaeological dig found the foundations of Upper Canada's first parliament buildings, burned by American forces in April 1813. The site later held a jail and a car wash before its 2000 rediscovery.