If you stand at the corner of Sainte-Catherine and Saint-Laurent today, you’ll see glass towers, trendy restaurants, and the hum of festival stages. But not long ago, this was the pulsing heart of a district renowned across North America for its liquor, jazz, burlesque, gambling, and brothels. What now feels sleek and sanitized was once gloriously chaotic, buzzing with late-night neon, scandalous headlines, and a constant rhythm of pleasure-seeking.
The Red Light District wasn’t a historical footnote or a shadowy corner of the city. It was a defining force in Montréal’s identity, drawing outsiders by the thousands. Artists and adventurers rubbed elbows with gangsters and gamblers. Dreamers came looking for escape or fortune, while outcasts found a rare sense of belonging. It was rowdy and raw, beautiful and bleak. And it deserves to be remembered in full, not just as legend, but as lived experience.
At MTL Detours, we created the Montréal’s Sin City: Golden Age Era & Red Light District walking tour not to glorify the city’s past or clean it up for comfort. Our goal is to understand it, to show the complicated forces at play, and to help curious visitors grasp how this rebellious and provocative district helped shape Montréal’s culture, reputation, and psyche.
When the Border Closed, Montréal Opened: The Prohibition Boom
In 1919, the United States went dry. With the ratification of the 18th Amendment, Prohibition began, cutting off legal access to alcohol for millions of Americans. Almost overnight, a tidal wave of thirsty travelers began looking north. Montréal, already known for its nightlife and laissez-faire spirit, became the closest and most attractive destination for Americans eager to keep the party going.
Though Canada flirted with its own temperance laws, Québec repealed its restrictions quickly, positioning Montréal as an unrepentant oasis. The city welcomed the influx with enthusiasm. Trains from New York and Boston arrived daily, packed with tourists chasing cocktails, cabaret, and carefree evenings. Boats pulled into the port with elegant guests, while automobiles lined up at the border, engines humming with anticipation.
This wasn’t just about alcohol. Prohibition poured gasoline on an already simmering entertainment scene. New clubs and bars opened at a rapid pace. Criminal networks flourished in the shadows, supplying contraband and setting up shop in the city’s underbelly. Jazz musicians found steady gigs and enthusiastic crowds. And sex workers, long part of Montréal’s hidden economy, suddenly found business booming with high-paying clients who crossed the border for a good time.go.
The Jazz Explosion
By the 1920s and ’30s, Montréal had earned its place as one of North America’s premier jazz destinations. Saint-Laurent Boulevard, known as “The Main,” became a pulsing artery of music, drawing talent from the world’s top jazz cities. Harlem, New Orleans, and Chicago sent their best, knowing that Montréal promised not only money, but respect and admiration.
Some of the biggest names in jazz took the stage here:
- Louis Armstrong, with his signature gravelly voice and trumpet brilliance, electrified local audiences.
- Billie Holiday and Ella Fitzgerald captivated smoke-filled clubs with performances that left listeners spellbound.
- Dizzy Gillespie, Cab Calloway, and Fats Waller lit up Montréal nights, often turning gigs into all-night affairs.
And then there was Oscar Peterson, Montréal’s own. Born in Little Burgundy, Peterson was still a teenager when he began playing local venues. His career would soar internationally, but his roots were planted deep in the soil of the city’s jazz scene.
At the heart of this movement was Rockhead’s Paradise, founded by Rufus Rockhead, a trailblazing Black entrepreneur and former railway porter. His club was the first Black-owned nightclub in Montréal and a sanctuary for African American performers who often faced discrimination elsewhere. Here, they were stars.
Other venues flourished too: Café St-Michel pulsed with swing and rhythm, while Club Montmartre offered glamour and glitz with its chorus girls, roulette tables, and tuxedoed patrons. Together, these clubs turned Montréal into a jazz capital, rivaled only by the likes of New York and Chicago.
Burlesque and Cabaret
If jazz gave the city its sound, burlesque gave it its sparkle. And no performer shone brighter than Lili St. Cyr. Draped in feathers, furs, and pearls, she didn’t just strip—she performed. Her acts were theatrical, sensual, and dripping with Old Hollywood glamour. One of her most iconic routines involved bathing in a giant champagne glass. Another, her famed bubble bath number at the Gayety Theatre, provoked headlines and outrage in equal measure.
City officials tried repeatedly to shut her down, labeling her acts immoral and indecent. But Lili St. Cyr was unstoppable, and crowds adored her for it. Her popularity made her a symbol of the era’s contradictions: scandalized on the front page, celebrated on the marquee.
Other performers brought wit, music, and subversive charm to the stage. Some shows combined comedy sketches with risqué dances. Others leaned into Parisian-style cabaret, where champagne and satire flowed in equal measure. For many locals and out-of-towners, a night at the cabaret was a rite of passage. It was where fantasy met rebellion, and Montréal fully embraced both.
The Underworld: Gambling, Mafia, and Crime
The Red Light District was built on vice—and vice was big business. Illegal gambling flourished behind unmarked doors and velvet curtains. Backroom poker games, hidden slot machines, and underground betting operations brought in staggering sums of money. Police often looked the other way, especially when the right palms were greased.
Among the most notorious figures was Harry Davis, Montréal’s self-proclaimed “king of the gamblers.” His empire spanned several establishments, and his assassination in 1946 shocked the city. His murder sparked a wave of police crackdowns but also revealed just how deep-rooted corruption had become.
Benny Allen, another gambling titan, made his fortune on horse racing and high-stakes card games. He operated with a blend of charm and cunning, keeping one foot in high society and the other in the criminal world.
By the mid-20th century, the Cotroni crime family had entrenched itself in every corner of the city’s underground economy. From brothels and betting parlors to extortion rackets, they held the keys to Montréal’s darker dealings. Their influence reached deep into police precincts and city hall. Businesses that paid for protection thrived; those that didn’t were often raided or mysteriously shut down.
The Morality Squad and the “Clean-Up”
As international attention on Montréal grew, Mayor Jean Drapeau took aim at the city’s seedy reputation. In the 1950s, he formed a dedicated morality squad to “clean up” vice and restore civic respectability. Their mission: eliminate gambling, shut down strip clubs, and impose order on the city’s nightlife.
But this wasn’t a crusade of equal justice. Enforcement was often selective. Some clubs—particularly those that paid protection money or had political allies—continued operating discreetly. Others became easy targets for public raids and media spectacle.
Despite the inconsistencies, pressure from the city, church groups, and moral reformers intensified. Club owners began closing or going underground. By the late 1950s, the wild, freewheeling spirit of the Red Light District had dimmed. Montréal was beginning its transformation into a city with a polished surface and buried secrets.
The Dozois Plan: Demolishing History
Moral pressure may have weakened the district, but it was the Dozois Plan that delivered the final blow. In 1957, Mayor Drapeau and his urban planning allies unveiled a redevelopment scheme based on the Dozois Report, a document that branded the Red Light’s historic core as a slum in need of elimination.
Entire blocks were expropriated and flattened. Brothels, vaudeville houses, jazz clubs, and cheap hotels disappeared almost overnight. Bulldozers rolled through streets once filled with music and mischief. In their place rose sterile low-income housing projects, many of which lacked the soul and charm of what had come before.
This was not just a neighborhood cleanup—it was cultural erasure. The very buildings that told the story of a unique urban identity were removed from the map, and with them, a chapter of Montréal’s boldest history.
Sex Work in Context
Throughout the Red Light era, sex work was not hidden in the shadows — it was part of the street-level reality of Sainte-Catherine, Saint-Laurent, and the surrounding blocks. In rooming houses above bars, behind unmarked doors near the port, and inside the city’s better-known maisons de tolérance, sex workers operated in plain sight. Some were independent. Others worked in brothels run by madams or connected to nightclubs that offered more than just music. They served dockworkers, soldiers, businessmen, tourists, and locals alike.
The work was precarious, often dangerous, and heavily policed. But it was also a form of income when few options were available, especially for poor and working-class women, single mothers, and recent arrivals to the city. The Red Light District functioned as a survival zone for some and a lucrative industry for others. Like the jazz scene and the cabarets, it existed within a network of unspoken rules, payoffs, and protection.
It’s a complex and layered subject, presented with care, context, and historical grounding — never for spectacle or shock. Rather than being glossed over or dramatized, it’s explored as part of the wider forces that shaped this neighbourhood and the city itself. The topic is told truthfully and respectfully by informed, professional guides who know the streets they walk and the histories they hold.
Why It Still Matters
Today, the Quartier des Spectacles covers much of the old Red Light District. It’s home to world-renowned festivals, cultural centers, and sleek condo towers. The city’s official story here is one of art, light, and reinvention. But if you know where to look, the bones of the old district remain. Faded ghost signs on brick walls. Alleyways with whispered pasts. Corners where once stood burlesque palaces or illicit casinos. The past doesn’t vanish; it lingers beneath the surface, waiting to be noticed.
The Montréal’s Sin City: Golden Age Era & Red Light District walking tour invites curiosity and reflection, offering a deeper look at the people, places, and forces that shaped this neighbourhood. Guided by licensed professionals, the tour connects the glamour and grit of the past to the city as it stands today — layered, complicated, and still full of stories.
Did You Know?
- Lili St. Cyr was once arrested mid-show — for bathing onstage in a champagne glass tub.
- Montréal’s Red Light was home to Canada’s first Black-owned nightclub: Rockhead’s Paradise.
- The Gayety Theatre regularly drew more crowds than the city’s opera houses.
- The Cotroni crime family had influence stretching into local politics and the police.
- Entire blocks of the Red Light were flattened in the 1950s under the guise of “urban renewal.”
- Montréal was once called “Sin City North” by American newspapers during Prohibition.
- Raids by the morality squad were often tipped off — unless you paid the right people.
An Invitation
If you’re curious enough to want more than polite postcard history, come walk with us. If you want to understand how this one square mile of Montréal helped forge its rebellious spirit, creative fire, and complicated legacy, this is the tour for you.
You’ll hear about the dancers and doormen, the crime bosses and jazz legends, the cops and cabaret queens. You’ll see how a city once known as the “Paris of the North” earned — and eventually lost — that title through its fearless embrace of pleasure, freedom, and spectacle.
And when the tour ends, you’ll leave with something more than just facts. You’ll carry a richer, sharper, and more human understanding of Montréal.
Because history isn’t always neat. But it’s always worth remembering.
Ready to explore Montréal’s untold stories?
Book the Montréal’s Sin City: Golden Age Era & Red Light District Walking Tour and see the city from a whole new angle. Discover where jazz legends played, cabarets dazzled, and a hidden history unfolded in the streets just beneath your feet.
About MTL Detours
MTL Detours is a locally owned and operated tour company offering intimate, story-rich walking tours led by passionate, professional guides. With a focus on Montréal’s character, history, and hidden gems, our small-group experiences go beyond the postcard version of the city to reveal what makes it truly unforgettable..
