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

  • 2 Hours
  • Max Guests: 10
  • 4:30pm
  • Fridays + Saturdays
  • Language: English
Viator Experience Award Winner 2023

Our Old Montreal walking tour was named as one of the Top 20 Experiences in Canada!

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 and we quickly became known as “Sin City” and “Paris of the North”. Thirsty folk, particularly Americans, flocked to Montreal to savour in the notorious nightlife, anything goes attitudes and raucous times. Our cabarets and Jazz clubs were famous and attracted talented musicians the likes of Ella Fitzgerald, Billie Holiday, Duke Ellington, Louis Armstrong and Count Basie, amongst others. Brothels, crime and bootlegging were rampant. 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!

* 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. 

Price Includes

Price Excludes

  • Your certified guide’s expertise as a local Montrealer
  • A personal list of recommendations for things to see, do, and eat in Montreal
  • A unique parting gift
  • Gratuities (recommended – merci!) — Although optional, a tip/gratuity for your guide is customary and very appreciated.

Tour Highlights

  • Exclusive small group of only 10 people makes for an unforgettable personal, informative and engaging experience!
  • Receive extras like our carefully curated list of recommendations and unique parting gift.
  • Get insider tips from your Montreal certified guide and their personal recommendations on where to eat, shop, and explore
  • Enjoy the engaging tour experience that comes with an intimate group size and passionate interactive guides

What We'll See On This Walking Tour

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 MEM – Centre des mémoires montréalaises, where we’ll set out to explore the city’s sin city era and golden age.

Our first stop will be the old 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.

Meeting Point

MEM – Centre des mémoires montréalaises

Your MTL Detours guide will meet you inside the MEM – Centre des mémoires montréalaises entrance. Go to the 2nd floor and wait for your guide outside the “dépanneur”.

Our meeting location is a short walk from the Saint-Laurent metro station (subway) on the Green metro line.

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.

Tour ends in the Quartier Latin, in the vicinity of Saint-Denis St. and De Maisonneuve Blvd.

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Participation requirements

This tour has an age minimum of 18 years old. Due to the mature and adult-oriented content, this tour is not suitable for minors under 18 years old. 

Not wheelchair accessible and not suitable for guests with mobility restrictions or serious health issues. Please inquire about the possibility of booking a private tour.

Places to sit and rest are very limited.

What to Bring

  • A camera or cell phone for taking photos
  • Water to stay hydrated
  • Weather-appropriate clothing, which may include:
    • A hat, sunscreen, sunglasses
    • Umbrella or poncho
  • As this is a walking tour, comfy footwear is essential!

About your guide

All MTL Detours guides are trained, certified, and licensed with the Institut de tourisme et d’hôtellerie du Québec and the Association professionnelle des guides touristiques, as required by the City of Montreal.

Check out our About Us for more info on each of our amazing guides!

What language is my tour in?

Our walking tours are offered in English by default. If you’re looking for a tour in French, please contact us or check our private tours option to make arrangements. Merci beaucoup!

What is your minimum age?

The minimum age to attend the Sin City tour is 18 years old. Due to the mature and adult-oriented content, this tour is not suitable for minors under 18 years old. 

Does weather affect the tour?

This tour runs in all weather – rain, shine, or snow! However, we occasionally have to cancel a tour in the event of extreme or violent weather (severe thunderstorms, freezing rain, high winds, or major snowstorm, for example). Should this occur, you will be offered another date or a full refund. Please monitor your messages/email if inclement weather is expected.

How should I dress?

Please dress appropriately for the weather conditions! This tour is entirely outdoors.

Cancellation policy

Our tours are 100% refundable up to 24 hours before the tour start time. Please be mindful that the later you wait to cancel, the harder it is for us to fill your spots. If you cancel less than 24 hours ahead of time or do not show up for the date and time that you booked, unfortunately, any sums paid will be 100% non-refundable. No-shows, bookings for incorrect dates/times and late arrivals are not eligible for refunds. We can try to fit you onto another tour, pending availability, but cannot guarantee this option. If you can’t make it, please contact us in advance to notify of your absence. For PRIVATE tours, the cancellation policy is 72 hours.


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