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At Torontoist, Jamie Bradburn's Historicist feature looks at the St. Charles Tavern's transition from cocktail lounge through Chinese restaurant to gay bar.

“Meet me under the clock”—for several decades, it was the slogan of the St. Charles Tavern. While it began in the early 1950s as a cocktail lounge owned by a prominent local horse breeder, the St. Charles gradually became one of the city’s most prominent gay bars, thanks to a combination of location and unintended consequences of Ontario’s liquor laws.

The clock tower above 484-488 Yonge was built as part of Fire Hall Number Three, which operated from the early 1870s until a new hall was erected on Grosvenor Street during the 1920s. Many tenants filled the space over the next three decades, including a bicycle shop, and a succession of car dealers who sold North American (GM, Kaiser, Hudson) and British (Austin, Morris) vehicles.

Among the most newsworthy incidents during this period was a fire which struck the second floor Metropolitan Gallery of Fine Arts in January 1940. The blaze damaged several paintings which, ironically, were brought from Europe to prevent damage during the Second World War. Among the major losses was 17th century Dutch painter Ferdinand Bol’s “Handwriting on the Wall.”

The site soon caught the eye of Charles Hemstead. From a childhood stint as a newsboy at Bathurst and King, Hemstead built a fortune on real estate investments, including several downtown hotels and taverns. Horses were his passion, as he operated several breeding farms which produced prize-winning stallions at several country fairs. Hemstead’s most notable horse was Paolita, who beat the longest odds in two decades to win the 1943 King’s Plate (currently the Queen’s Plate). Paolita was such a long shot that $2 bets paid out $76.50.
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