Waterloo's Forgotten Criminal Past: Prohibition, Gangsters & Bootlegging Skip to main content

The Waterloo region is many things. When asked, people often boast about its two highly sought-after universities. Others talk about the town’s vibrant tech scene that attracts international business and rivals Silicon Valley. But there’s one piece of history about this town that many do not know of though and that’s its heritage of being a gangster-filled, booze-smuggling, and bootlegger hotspot during the Prohibition era.

A Mostly Forgotten Heritage

This was a time when gunfire could be heard in the streets, titans of industry knowingly interacted with the criminal underworld, and police raids were normal. This time period was that of the Prohibition when the United States banned all alcohol production and sale while Ontario remained more lenient in their rules.

Ontario voters opted to keep the production of alcohol legal and even allowed the substance to be prescribed for medical purposes when a doctor deemed it necessary. In context of Waterloo, the town’s folk were even more tolerant of the substance because they knew it substantially affected their economy by preserving the operations of the famous Kuntz Brewery and Seagrams Distillery. As such, the Waterloo region became the apex to a bootlegging triangle of operations stretching between Waterloo, Hamilton, and Toronto according to authors James Dubro and Robin Rowland.
Previously home to one of North America’s most prolific distilleries, once a key player in the illegal smuggling of alcohol to the United States, the Seagram Distillery now houses lux condo living space following renovations and restorations.

To Waterloo, Prohibition only signalled to those adventurous enough to chance the law and the criminal underworld an opportunity to amass incredible wealth by smuggling and selling the prohibited substance south of the border. With the distillery and brewery in full production, all that had to be taken care of was the logistics of shipping quantities of all shapes and sizes to the US where it could be sold and consumed in private at a premium cost. As such, Waterloo attracted more than just run-in-the-mill thugs; on the contrary, Waterloo was visited by infamous names like Perri and Al Capone as it stood as the starting point for vast amounts of alcohol that would splash into the thirsty United States.

Whereas a bottle of Seagram’s Whiskey could be purchased for $2.50 in Ontario, that same bottle could fetch $10 in Michigan. Or, if a bootlegger was able to get a case of the same whiskey all the way to New York City, they could see their initial $49 investment grow to $150.

Profit margins like these definitely did not go unnoticed, neither by bootleggers looking to make a small fortune or by the governments of both Canada and the US for obvious reasons.

A Town Affair

The producers and occasional restaurant caught serving beer with uncapped alcohol levels were not the only businesses to get involved though. In fact, some of the establishments that played large roles in Waterloo’s entrepreneurial Prohibition experiences still exist today. Take Waterloo’s beloved Heuther Hotel for instance. Today, pub-dwellers are delighted with two restaurants, a pool lounge, a formidable summer patio, a specialty cafe, and a jazz room. However, less than a century ago, the inner-workings of the hotel (named The Kent Hotel at the time) served a wholly different purpose.

Home to the Lion Brewery Restaurant, Barley Works restaurant, Café 1842, and the Jazz Room, the Heuther Hotel really does have something ‘for everyone’. Explorers can enjoy a latte on the ground floor, eat at 1 of the two full-service restaurants serving craft beer made in the same location, play billiards between either restaurant, and finally enjoy live jazz in the Jazz Room on select nights. To top it all off, the Heuther’s patio is by far the place to be during the summer where those looking for beverages can enjoy The Lion Brewery, founded in 1842 by the Huether family and now operated and preserved by the Adlys family, is one of the oldest breweries in Canada.

During the 1960’s, city workers discovered a tunnel connecting a basement door within the Heuther Hotel to the corner of King & Princess St. where night clubs and clothing stores exist today but back then would have existed something called the Dominion Tire Collection. Although disguised to appear like any other car mechanic garage, this establishment specialized in smuggling alcohol in the bodywork of vehicles as a way to covertly transport the goods down south.

(The Kent Hotel, renamed the Heuther Hotel today)

(The Dominion Tire Collection, now home to Stark & Perri among numerous other businesses)

Waterloo’s Underground Connections (Literally)

Using liquor and beer conceived from the Seagrams Distillery, Kuntz Brewery, or in-house Lions Brewery (a brewery still in operation today), transporting the alcohol from hotel to the garage could go on unnoticed by nature of the underground passageway. Once at the garage, the bottles and containers would be hidden inside of specially customized car parts and bodywork that could be ‘sold’ and shipped to customers in the United States.

Nowadays, the Dominion Tire Collection no longer exists but in its place stands Stark & Perri, a pub coyly named after its Prohibition-heritage paying homage to the infamous bootlegger Rocco Perri. Guests enter the basement pub via a wood-panelled staircase and treated to reclaimed industrial look with accents of old books on the wall and leather-tufted recliners.

Despite not being the garage it used to be though, the pub’s owner was still able to vouch for the building’s criminal history when he found vintage car parts riddled with bullets buried under what is now the pub’s outdoor patio. From gangsters and guns to upscale cocktails and pizza, the Dominion Tire Collection lives on – just in a different form with a notably different atmosphere.

Located in former rum-runner territory, the location of this pub was allegedly used for boot-legging during the Prohibition era. As the story goes, those involved in the operation installed fake gas tanks to cars and used those tanks to smuggle and transport alcohol south of the border. They even formed a business called the Dominion Tire Company to make everything sound even better and ended up even sheltering one of Al Capone’s many cars in the vicinity after forming deep ties in the industries.Today, Stark & Perri is the brainchild between pub-style nightlife and good cooking. Between the old books on the wall, tufted leather sofas, spread out layout, and excellent (much less huge!) pizzas, this pub has something for everyone.

A Legacy Still Celebrated – Just in a Different Form

It’s stories like these that bring new life and cast amusingly different lights on the venues we love to frequent in a town we like so much. The next time you find yourself drinking a cold one on a hot summer day on the Heuther’s patio, you may find yourself gazing across the street and imagining the bootleggers working quietly and quickly through the night. On the contrary, perhaps you might smile the next time you pass the Seagrams Lofts condo complex and think of a previous time when less-than-savoury business deals were being hashed out between titans of industry and criminal kingpins.

The fact that multiple of these locations still stand today is also a treat for informed present-day residents and those passing through the town. Sharing a pint on the corner of King & Princess St. in Stark & Perri or passing by the Seagram Lofts becomes all the more exciting and interesting when the region’s history as a bootlegging destination is remembered. Understanding this history also perhaps sheds light on Waterloo’s commitment and strong enjoyment for its multiple craft breweries throughout the region.

Our Germanic heritage may require a Ms. Octoberfest and a sea of lederhosen, but our dark history of working the Prohibition to our advantage demands nothing more than a pint of well-crafted and borderline illegally good tasting beer. Considering our history, its no surprise producers like the Abe Erb Brewing Company and the Descendants Beer & Beverage Co. continue to flourish.

Preaching a trifecta of integrity, solidarity, and craftsmanship, this craft brewery is a must-visit. Founded in commemoration of Abraham and John Era, two Waterloo Mennonites of the 19th century, Abe Erb serves up an excellent of house-brewed craft beers, imaginative cocktails, and delectable food. Every batch is custom and can only be accessed via its in-house beer shop or its restaurant portion of course.

Nowadays, Waterloo residents may buy their alcohol legally from its various LCBO locations and consume it without fear of legal recourse but many of our heritage buildings stand strong, tall, and proud reminding us of the intriguing stories all around us. For more stories or the chance to tell your own, Map Your City is the best way to explore the cities around you while shining the spotlight on those locations and experiences too good not to share with others

We designed Map Your City to help you to connect, engage, and tell your stories at all the places that matter to your community.

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