Montreal's Sin City Era + Golden Age Walking Tour by MTL Detours
Overview
Available languages
Mobile ticket
While prohibition put a damper on the early 20th century in the USA and elsewhere in Canada, the booze kept flowing freely in Montreal and it quickly became known as “Sin City” and “Paris of the North”. Visitors flocked here to indulge in the notorious nightlife and raucous times. Whatever the vice or pleasure, it could be found in Montreal. Our cabarets and jazz clubs attracted talented musicians the likes of Ella Fitzgerald and Louis Armstrong, amongst others. This history walking tour will enthrall you with stories about local institutions and the cast of characters that frequented them. Performers, mobsters, street workers, and cops all rubbed elbows in the old Red Light District. Hear about the transformation of the district into the Quartier des Spectacles: home to Montreal's world-famous International Jazz Festival. Join MTL Detours to learn about this era in the unique city of Montreal! Note that portions of this tour goes through off-the-beaten path and non-touristy areas.
Additional Info
Service animals allowed
Public transportation options are available nearby
Suitable for all physical fitness levels
Minimum age to attend is 18+ years old.
This tour is owned and operated by MTL Detours Walking Tours mtldetours.ca - the same team behind the bestselling "Explore Old Montreal" walking tour.
Most of the tour is walking or standing with limited places to sit.
Not recommended for travelers with mobility restrictions or other impairments
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
Saint Laurent Boulevard
Meet your guide near the intersection of St. Laurent Blvd./Ste. Catherine St., right in the heart of Montreal's old Red Light District. Explore the surrounding vicinity and hear the fascinating stories of the illicit activities that used to mark this area of town.
Quartier des Spectacles
Explore the Quartier des Spectacles - Montreal's Entertainment District. Following prohibition, the booze flowed freely in this area and it became a hotspot for cabarets and nightclubs. Hear the riveting stories of Montreal nights from the 1920s to the 1950s.
What‘s Included
A list of recommendations of things to see/do/eat in Montreal curated by MTL Detours founder Lesley
MTL Detours, founded in Montreal, is a 100% locally owned + operated small independent tour company
Exclusive small-group of only 10 people
Unique parting gifts
Local, certified guide with the mandatory city guide permit
Gratuities - tips are optional but very appreciated
Hotel pick-up or drop-off. All guests must make their way to our meeting location on their own.
Options
Montreal's Sin City Era + Golden Age Walking Tour by MTL Detours
Reviews
11 reviews
Total reviews and rating from Viator & Tripadvisor
Informative and Fun
Rose J,May 8, 2025
- Review from Viator
5.00Our tour guide was the absolute best. She was very knowledgeable in Montreal history. We walked around what was once the Red Light District and she pointed out buildings and gave us amazing facts and tidbits of that era in Montreal. I really enjoyed this tour and would take it again.
Isabelle is a wonderful...
Amie S,May 4, 2025
- Review from Viator
5.00Isabelle is a wonderful guide! Engaging, knowledgeable and clear. The pace of the tour was perfect with a great balance of historical and neighborhood info.
Do this tour
O2794BKrobertp,Jul 13, 2024
- Review from Tripadvisor
5.00Super great tour of Montreal’s past and progress since Loved the guides joy of the city. Great walking tour of the evolution of what gave and gives Montréal its “it” factor
Montreal and its frosty side
mariejos ec884,Jun 2, 2024
- Review from Tripadvisor
5.00My colleagues and I loved our guided tour on the theme of "the city of sin and the golden age of Montreal". Our guide Isabelle made us relive this vibrant era on foot, in images and in music! A real interactive outdoor history lesson!
One of the best walking tours I have done
sherrysF4262GU,May 4, 2024
- Review from Tripadvisor
5.00An excellent tour chockfull of information, so many wonderful interesting insights into seemingly ordinary buildings. Very much appreciated the final gifts at the end as well! One of the best walking tours I have ever been on.
Best walking tour
1122diesel,May 4, 2024
- Review from Tripadvisor
5.00Our tour guide was incredible. So much knowledge and a deep understanding of many eras and moments in Montreal’s colourful history! Will recommend to any friend who visits your beautiful city! Well done! ❤️
A hidden side of Montreal!!!
Jo R,Apr 24, 2024
- Review from Viator
5.00Great tour guide!!! So enthusiastic and full of insider info. I’m from Montreal and I learned so much about historical characters and shenanigans!!! From the jazz scene to prohibition and the renowned bank robber machine gun Molly! I would do it again!!!
Super Interesting!
suzakabruiserg,Apr 8, 2024
- Review from Tripadvisor
5.00Very engaging and friendly guide. Tour was super interesting and filled with lots of history on Montreal's seedy underside.
A truly unique tour!
Kim C,Apr 7, 2024
- Review from Viator
5.00Super-unique tour all about Montreal’s ( somewhat) hidden history. The most knowledgeable and passionate guide helped it all come to life with the help of the MEM ( starting point of the tour), historic landmarks, photographs and even music from the era. Really interesting tour!
I loved it and recommend this walking tour to anyone else
petervI2920RZ,Apr 7, 2024
- Review from Tripadvisor
5.00I had such a good time on this waking tour. I thought I knew a lot about the Sin City nature of Montreal, as there have been books on it etc., but the guide was so knowledgeable about the area there wasn't enough time for her to tell us everything she knew. Most of it was new to me, almost all of it. I'd recommend this to anyone, tourists and Montrealers alike, anyone who wants to know a bit more about this quartier and some of the rich history of Montreal.
From CA$47.00
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