Montreal’s Sin City Golden Age Era & The Red Light District

While prohibition and the temperance movement put a damper on the early 20th century in the United States and elsewhere in Canada, the booze kept flowing freely in Montreal. This led to the city quickly becoming known as “Sin City” and the “Paris of the North.” Thirsty folk, particularly Americans, flocked to Montreal to savour its notorious nightlife, anything-goes attitude, and raucous times. Our cabarets and jazz clubs were famous and attracted talented musicians like Ella Fitzgerald, Billie Holiday, Duke Ellington, Louis Armstrong, and Count Basie, among others. The Montreal Red Light District was infamous for its rampant brothels, crime, and bootlegging. Whatever the vice or pleasure, it could be found in Montreal. Dancers, singers, mobsters, sex workers, bookies, musicians, strippers, gamblers, and cops all rubbed elbows in the old Red Light District. Join us to learn about this entertaining era of history in the unique city of Montreal. 

* Note that portions of this tour goes through off-the-beaten path and non-touristy areas.

* A portion of ticket proceeds will be donated to Stella Montreal. Stella’s primary mission is to improve the quality of life and working conditions for woman-identified sex workers.

Welcome to our Montreal’s Sin City Golden Age Era & The Red Light District tour, where we’ll delve deep into the fascinating history of Montreal’s vibrant past. Our journey begins outside the Théâtre Saint-Denis where we’ll set out to explore the city’s sin city era and golden age.

Our first stop will be the old Montreal red-light district, once a bustling hub of vice and debauchery. Here, you’ll hear stories of the city’s notorious past, filled with speakeasies, brothels, and clandestine gambling dens. Learn about the colorful characters who populated these streets and the illicit activities that defined this era.

Continuing our walk, we’ll make our way to the Quartier des spectacles entertainment district, where Montreal’s vibrant cultural scene flourishes. Discover how this area has transformed over the years, from its roots as a hub of cabarets and jazz clubs to its present-day status as a center for world-class festivals and performances.

We’ll stroll down Sainte-Catherine Street, once known as Montreal’s main shopping thoroughfare and a hotspot for nightlife during the city’s sin city era. Hear tales of prohibition-era establishments and the rise of organized crime in Montreal, including legendary figures like the infamous Cotroni crime family.

Our journey will take us along Saint-Laurent Boulevard, a historic artery that has long been synonymous with Montreal’s cultural diversity and nightlife. Hear about the rich tapestry of cultures that have shaped this vibrant neighborhood, from its early days as a gathering place for immigrants to its emergence as a center for art, music, and culinary delights.

Throughout the tour, our knowledgeable guides will regale you with captivating stories and anecdotes, shedding light on Montreal’s complex and colorful history. From the heights of its golden age to the depths of its sin city reputation, this tour offers a fascinating glimpse into a bygone era that continues to resonate in the city’s identity today. Join us as we uncover the secrets of Montreal’s past and celebrate the spirit of resilience and creativity that defines this dynamic metropolis.

Théâtre Saint-Denis 1594, rue Saint-Denis, Montréal

Meet your MTL Detours guide on the sidwalk outside the entrance of Théâtre Saint-Denis.  Our meeting location is a short walk from the Berri-UQAM metro station (subway) on the Green/Orange/Yellow metro lines.

Please note, we ask that all guests arrive at least 10 minutes before the tour start time. As our tours begin on time, latecomers may not be able to join the tour.