Looking back at the 5 most historic bars in Toronto

Explore Toronto’s rich past through the lens of its most historic bars. These iconic establishments have been witness to countless stories, celebrations, and the city’s cultural evolution.

Join us on a journey through time as we revisit these five bars that have helped to shapeToronto’s history.

The Wheat Sheaf


From Great War soldiers, to hippies, all the way up to millennial’s, The Wheat Sheaf has poured one out for just about every generation this city has ever seen. Older than Canada itself, this pre-confederate bar has been a steadfast presence, surviving fires, Prohibition, and urban development.  Initially a men’s-only spot until 1969, the building, , holds a mysterious tale of a tunnel connecting it to Fort York, though skeptics doubt its existence.

The Miller Tavern

Opened as the York Mills Hotel in 1857, the Miller Tavern was originally designed as a road house for travelers looking for a pint and a place to rest their horses. In the 20th century it took a debaucherous turn amongst high school students as the Jolly Miller. Now, the Miller Tavern is Hoggs Hollow’s most historic seafood restaurant.

The Maple Leaf Tavern 

Maple Leaf Tavern (Dan Seguin, Good Hood, 2015)

Before the people of Toronto knew Great War, they knew the Maple Leaf Tavern. Opening in 1910, this bar was once known as the “kick and stab” for its less than inviting atmosphere. After undergoing a full remodel, the Maple Leaf Tavern is now one of the city’s classier joints. Serving steakhouse fare and a real community tavern atmosphere, this place is far from its days as a down and out drinking hall.

The Gladstone Hotel

The Gladstone (James Salman, 1952)

Opened in 1899, this turn of the century hotel was the safest in Toronto. Smack dab in the centre of Parkdale, this bar was filled with traveling workers and family members that were visiting the city. The Melody Bar was opened in the Gladstone lobby in the 50’s. The reimagined Gladstone House continues its commitment to culture, art, and diversity, preserving the building’s rich history and iconic original architecture.

The Black Bull

The Black Bull (City of Toronto Archives, 1972)

A Toronto landmark since 1833, this bar has arguably been around longer than any on this list. The reason this bar has been excluded for the title of Toronto’s oldest bar is that it was named the Clifton House for several decades before changing back to its original name, The Black Bull. A boarding house with a rough reputation, this was a meeting spot for farmers and city dwellers to relax over a pint or two. Today it sports a massive patio where Queen Westers come to sip sangria on Saturday afternoons.