Raise a Glass to History: 12 Ways to Experience Prohibition Week in Windsor
Step Into the Roaring Twenties During Prohibition Week in Windsor August 17th to 23rd!
What if you could travel back to the Roaring Twenties without leaving Windsor?Β Prohibition Week transforms Windsor into a celebration of one of the most fascinating eras in Windsor’s history. During the 1920s, our region became world-famous as a hub for rum-running, supplying Canadian whisky across the Detroit River during American Prohibition. Today, that remarkable history comes alive through immersive tours, theatrical experiences, brewery tastings, river cruises, special film screenings, heritage walks, exclusive shopping promotions and much more.
Whether you’re a history enthusiast, craft beer lover, movie buff or simply looking for a unique summer adventure, Prohibition Week is your invitation to experience Windsor’s legendary past while supporting the local businesses that continue to shape its vibrant culture.
Raise a Glass with the Prohibition Pass
Created exclusively for Prohibition Week, this mobile-exclusive Barrels Bottles Brews Prohibition Pass lets you enjoy one complimentary tasting flight at each of our four Windsor craft breweries:
- Walkerville Brewery
- Chapter Two Brewing Co.
- Sandwich Brewing Co.
- Erie St. Brewery
Simply purchase your pass, receive it instantly by text and email and redeem your tasting flights between August 17th and 23rd.
Visit all four breweries during the week and you’ll even earn a prize from one participating brewery!
It’s the perfect opportunity to discover Windsor’s craft beer scene while celebrating the city that helped shape North America’s drinking history.
Unlock Windsor’s Small Business Speakeasy
Every great speakeasy has a secret password.
During Prohibition Week, participating local businesses are inviting visitors to whisper the password and unlock exclusive discounts available only during the celebration.
Stop in to the following businesses to discover unique local products and hidden treasures:
- Anchor Coffee House, 543 Lincoln Rd.
- Biblioasis Bookshop, 1520 Wyandotte St. East
- Chimczuk Museum Gift Shop, 401 Riverside Dr. West
- Cookie Bar, 1093 Drouillard Rd.
- Smudge Metaphysical Boutique & Botanica, 533 Lincoln Rd.
- Streetcar No. 351 Gift Shop, 780 Riverside Dr. West
- Urban Art Market, 548 Chilver Rd.
- Walkerville Relics, 571 Lincoln Rd.
- Whiskeyjack Boutique, 68 University Ave. West
Take A Sip Of The Past
Step back in time and raise a glass to Windsorβs Prohibition-era past duringΒ Prohibition Week taking placeΒ August 17th to 23rd. Throughout the week, the following eight local cocktail bars turn into play up their speakeasy vibes and will be serving up exclusive, prohibition-inspired creations that pay tribute to the cityβs fascinating history as a hub for bootlegging and cross-border spirits.
Participating ‘speakeasy’s’ include:
- ekΕ
- Erie St. Gastropub
- Funky Chow Kitchen
- Ikto Tiki
- Maiden Lane Wine & Cocktail Bar
- Thirsty Butler
- Vu Bar at Caesars Windsor
- WindsorEats
Whether youβre a cocktail enthusiast, a history buff, or simply looking for a unique night out, this is your chance to sip on a taste of the past while exploring some of Windsorβs most distinctive hidden gems. Visit each featured speakeasy, discover their signature Prohibition Week cocktail, and toast to the stories, secrets, and spirits that helped shape Windsorβs legendary legacy.
Experience Prohibition Where It Happened
Step into the places where history unfolded and explore the streets where it all happened.
Rum Runners Tour
You do not want to miss the special edition of the legendary Rum Runners Tour.
Step back in time and experience the thrill of Windsorβs Prohibition era with The Rum Runners Tour! This award-winning, adventure is your ticket to the Roaring Twenties, blending drama, comedy, and live music for an unforgettable journey through history.
Imagine yourself aboard a luxurious coach, guided by costumed characters who unveil the secrets of rum-running, infamous speakeasies, and the daring exploits of those who kept the spirits flowing during the dry years.
The highlight of your adventure? A visit to a recreated speakeasy where the legendary Bertha Thomas herself welcomes you. Savor a delicious hot meal while Bertha shares captivating stories of Hollywood stars and notorious gangsters. All the while, βFingersβ tickles the ivories, setting the perfect moodβbut watch out for those pesky police raids!
Monday August 17th β 5:30pm
Tickets: $75
Click hereΒ for details and to book your tickets.
Willistead Manor & Coach House Tours
Built in 1906 for Edward Chandler Walker, Willistead Manor stands as one of Windsor’s architectural treasures.
During Prohibition Week, visitors can tour this magnificent estate and explore the Coach House Historical Exhibition, where exhibits tell the story of Hiram Walker, the Walker family, the development of Walkerville, and Windsor’s enduring connection to Canada’s whisky industry. It’s the perfect complement to any Prohibition itinerary and offers fascinating insight into the people behind one of Canada’s most influential distilling families.
Monday August 17th 6-8pm & Tuesday August 18th 9-11am
Tickets: $3.50 at the door
Click hereΒ for details.
Free Day at Museum Windsor β Chimczuk Museum
Visitors are welcome to attend Museum Windsor during regular operating hours and enjoy free admission. No registration is required.
The Chimczuk Museum is a premier museum destination that houses permanent exhibits on the history of the Windsor area, the Original Peopleβs Culture and Legacy, and the development of The City of Windsor. The site also features a state-of-the-art Childrenβs Gallery and Learning Space with opportunities for hands-on exploration for our young and young at heart, two galleries for travelling and temporary exhibitions, and a gift shop with fantastic souvenirs for guests of all ages.
As part of prohibition week visitors will be able to take a seat at the original Abars Bar!
Tuesday August 18th β 10am-5pm
Admission is FREE!
Click hereΒ for details and to book your tickets.
Walkerville District Walking Tour
Discover the remarkable story of Hiram Walker and the company town that grew around one of Canada’s most famous distilleries.
The Walkerville District Walking Tour takes visitors through one of Windsor’s most beautiful historic neighbourhoods, highlighting the architecture, businesses, and people who helped shape the city’s identity. From elegant homes to historic commercial buildings, every stop reveals another piece of Windsor’s whisky legacy.
Wednesday August 19th β 6:30pm
Tickets: $5
Click hereΒ for details and to book your tickets.
J.P. Wiser’s Tour & Tasting
No conversation about Windsor and Prohibition would be complete without mentioning Canadian whisky.
During Prohibition Week, J.P. Wiser’s invites guests to experience one of Canada’s most iconic distilleries through guided tours and tastings that showcase more than 165 years of whisky-making excellence. Learn how whisky is crafted, hear stories from Windsor’s distilling past and enjoy tastings that celebrate one of Canada’s most recognized spirits.
It’s a must for whisky enthusiasts and anyone interested in learning why Windsor became synonymous with premium Canadian whisky.
Thursday August 20th β 11am, 1pm, 3pm, 5pm
Tickets: $12.50
Click hereΒ for details and to book your tickets.
Windsor Premier Cruises Prohibition Boat Cruise
Imagine cruising the same waters once used by rum-runners transporting whisky across the Detroit River.
The Windsor Premier Cruises Prohibition Boat Cruise offers guests an unforgettable evening on the river, complete with fascinating stories of Windsor’s bootlegging past, spectacular waterfront views, themed entertainment, and plenty of opportunities to soak up the atmosphere of the Roaring Twenties. It’s a chance to see Windsor’s history from the very waterway that made it famous.
Friday August 21st β 2pm
Tickets: $25
Click here for details and to book your tickets.
WIFF Screening of The Great Gatsby
The glamour of the Roaring Twenties comes to the big screen during a special WIFF screening of The Great Gatsby.
Whether you’re a fan of F. Scott Fitzgerald’s timeless story or simply love the fashion, music, and elegance of the Jazz Age, this screening is a wonderful way to immerse yourself in the spirit of the era that inspired Prohibition Week.
Come dressed in your finest 1920s attire and enjoy an evening celebrating one of literature’s most iconic tales.
Friday August 21st β 7pm
Tickets: $5
Click here for details and to book your tickets.
Riverfront Summer Series ~ Riverfront Speakeasy
Saturday August 22nd β 5pm-10pm
Legacy Beacon,Β Michael D. Hurst Legacy Park,Β Streetcar No. 351 and Windsor Sculpture Park
Step into another era as Riverfront Speakeasy transforms the waterfront into a stylish open-air experience inspired by Windsorβs Prohibition-era history, streetcar legacy, and vibrant arts scene. Stroll beneath cafΓ© lights as jazz musicians, vintage cars, illuminated sculptures, and surprise performances bring the park and sculpture garden to life. Discover hidden corners throughout the site featuring interactive art, fortune tellers, LIVE entertainment, and immersive experiences inspired by the glamour and intrigue of the 1920s.
REGISTER FOR THE CROSSROADS HISTORICAL GUIDE
Register for the free CROSSROADS HISTORICAL GUIDE β a non-downloading-needed digital pass that can guide you to stops across the region, including a special feature on the Prohibition History on Windsor and Essex County.
Register for free today at visitwindsoressex.com/CROSSROADS and the pass will be sent directly to your phone and email.
Use it to get guided from stop to stop β learn more about the sites β and answer unique trivia at each stop to learn more about the past, and how weβre using the heritage site today!
Build Your Perfect Prohibition Week Itinerary
There are countless ways to experience Prohibition Week, but here’s a couple of ideas:
- Start your morning with a tour of Willistead Manor then stop for a coffee and set off on a Small Business Speakeasy adventure.
- Visit one (or four!) breweries using your Prohibition Pass before heading to a river cruise or film screening.
- Then return another day to experience the Rum Runners Tour or a J.P. Wiser’s tasting
- Round out the week at the Riverfront Speakeasy.
No two itineraries have to be the same and that’s what makes Prohibition Week so much fun!Β
The secret’s out, and everyone’s invited!
Whether you’re sipping local craft beer, uncovering hidden shopping discounts, cruising the Detroit River, touring historic landmarks, enjoying live entertainment, or learning about the rum-runners who shaped our city’s identity, every experience offers gives you an opportunity to learn and celebrate!
Mark your calendar for Prohibition Week August 17th to 23rd, gather your crew and start planning your Prohibition Week adventure today: purchase your Prohibition Pass, unlock the Small Business Speakeasy, reserve your tickets for the week’s signature events, and discover why Windsor remains one of Canada’s most fascinating places to experience the legacy of Prohibition.
