Canada’s reputation as a squeaky-clean, friendly neighbour to the U.S. could go from nice to naughty if you consider its vices. From east to west, north to south, notorious characters and infamous landmarks expose a spicier side of Canada mostly forgotten in the past.
Looking back, Canadians could blame Americans for their criminal influence. Prohibition in the U.S. made Canada a profitable playground for rum runners and gangsters, like Al Capone. The infamous crime-syndicate leader visited cities like Windsor and Moose Jaw to facilitate his illegal shipments of booze, though he denied it when questioned by police.
“I don’t even know what street Canada is on,” he once quipped.
Meanwhile, the Chinatowns of Victoria and Vancouver hosted opium dens – sometimes opulent hangouts staffed by beautiful women who catered to both Chinese and non-Chinese patrons. In the east, Montreal’s joie de vivre made it a hub for lusty cabarets (more than 30 by the 1940s), scandalous burlesque acts and brothels.
Flash forward to current day Toronto where visitors can celebrate gluttony with food eating contests featuring gnocchi, poutine and more.
For a deeper look into Canada's illicit past, check out the gallery below and be sure to leave a comment if you've ever visited one of Canada's naughtiest destinations.
Canada's Naughtiest Destinations. Slideshow text follows for mobile readers.
Fan Tan Alley
Fan Tan Alley in Victoria’s Chinatown is recognized not only for being the narrowest street in Canada, but for its risqué past as home to opium dens, gambling and brothels. That was circa 1858. Today, those illicit pursuits have been replaced with shops and apartments, but tourists still come for a look at its wicked past.
Al Capone's Cabin Hideout
Al Capone slept here. The Chicago mobster and his crew hung out in the backwoods of Northern Ontario in the Bancroft area. The log cabin was hidden well out of sight, far from the prying eyes of lawmakers and rumour has it that there were escape tunnels, ready if things got too heated. When Capone wasn't hiding out in Bancroft, Ont., there are also claims he spent time in Moose Jaw, Sask. and Windsor, Ont.
Bombay Peggy’s Inn And Pub
If walls could talk, guests would blush at Bombay Peggy’s inn and pub in Dawson City, Yukon. In the early 1940s, Margaret Vera Dorval acquired the Gold Rush era building to open a brothel. It was derelict and crumbling until 1998, when it was bought and restored over 14 years. Rooms are now available for more virtuous visitors.
Ellen Paige's Old "Haunted" Brothel-Turned-House
Former brothels apparently make great homes. In 2008, actor Ellen Page (best known in the movie 'Juno') took up residence in a Victorian era one in Halifax. She told David Letterman it was haunted and complained the ghostly residents were stealing her stuff. She later told viewers that the house's microwave would turn on mysteriously at night during an interview with the BBC's Jonathan Ross.
Le Gaiety Nightclub
For seven years, Lili St. Cyr, the Minneapolis-born burlesque dancer, reigned supreme as the star performer at Montreal’s Le Gaiety nightclub, starting in 1944. Billed as the “Anatomic Bomb,” Montreal police came to see her under the guise of protecting the public. You can see the club façade at 535 St. Catherine Street West, but Lili left the building long ago.
The City Of Toronto
Gluttony is counted among the seven deadly sins. With that in mind, Toronto earns a top spot among sin cities for its plethora of competitive eating contests, like the Canadian Oyster Eating Championships at The Ceili Cottage. Hungry-types can book a spot at the table in search of food infamy at various showdowns across town at showdowns featuring poutine, spicy dosas, gnocchi, or burritos.
The Ottawa Hostel
Conditions in this former Ottawa jail, built in 1862, were appalling. Up to 150 prisoners were crammed into tiny cells under filthy, unsanitary conditions. In 1869, 5,000 citizens showed up for the hanging of Patrick J. Whelan, the assassin of politician Thomas D’Arcy McGee. Today, it’s a hostel, housing an international array of tourists wishing to spend a night in jail. It still has plenty of creep factor left with the original gallows and death row still intact.
The City Of Hamilton
Also known as "the steel capital of Canada", the city of Hamilton has a sinister past full of murderers, mob hits and femme fatales. All are the focus during a dark history walking tour, presented by Ghost Walks. It includes locations connected to Canada’s most famous murderess Evelyn Dick, charged with the death of her husband after his headless torso was discovered in 1946, and gangsters like crime boss Rocco Perri who was last seen in 1953.