Windsor, October is here and the calendar's already packed.
This week (Oct 1–8) Bert Kreischer brings his Permission to Party World Tour to The Colosseum at Caesars, UB40 takes the same stage a day later, and the Windsor Zombie Walk and Parade kicks off spooky season downtown. Add Oktoberfest celebrations, the Tart & Soul Butter Tart Festival, and live comedy from Windsor Laughs, and there's plenty to keep you busy.
Here's your full guide to the best of Windsor-Essex this week.

🎭 October 9, 10, 16, 17 & 18 – Dear Evan Hansen
Oct 9 8:00 PM • Oct 10 8:00 PM • Oct 16 8:00 PM • Oct 17 2:00 PM & 8:00 PM • Oct 18 2:00 PM | Capitol Theatre, 121 University Ave W, Windsor

A powerful musical about a teenager struggling to find where he belongs after a private letter unexpectedly pulls him into a life-changing misunderstanding. As the situation grows, he is forced to confront honesty, friendship, family, grief, and the consequences of being seen and heard. Featuring songs like Waving Through a Window, For Forever, and You Will Be Found. 🎶💙

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Windsor’s music scene is stacked this season—from techno nights and live summer DJ parties, there’s a sound for every vibe and every night out.

🎭 October 1 – OnStage: CBC’s Tom Allen: A Poe Cabaret
Capitol Theatre
Experience orchestral music from a unique perspective with this immersive OnStage concert, where audiences are invited to sit directly on stage alongside the musicians

☕ October 2 – Café Concert: CBC’s Tom Allen: A Poe Cabaret
Capitol Theatre
Enjoy a relaxed and intimate morning with the Windsor Symphony Orchestra as audiences experience live music directly from the stage alongside complimentary coffee and tea.

🎶 October 2 – Monarch Cafe Series – Songs and Stories in the Round
See event details | The Bank Theatre
Experience a Nashville Bluebird Cafe-style evening with artist-in-residence Justin Latam joined by three local and touring musicians.

🪩 October 2 – The Australian Bee Gees Show – A Tribute to the Bee Gees
Chrysler Theatre
Travel from Las Vegas to the world of disco as The Australian Bee Gees Show recreates the sound and spirit of the legendary Bee Gees in a live tribute concert.

🎶 October 2 – UB40 at Caesars Windsor
8:00 PM | The Colosseum at Caesars Windsor
UB40 is a British reggae-pop group known for its extensive recording career, more than 100 million albums sold globally.

🎤 October 3 – Creat1ve City Live
9:00 PM | Joywave
Celebrate Young Creat1ve’s album release with a night of live performances, special guests, and the official midnight release of his newest album.

🎻 October 3 – Classical in the Concrete
6:00 PM | Pelissier Street Parking Garage
Experience the Windsor Symphony Orchestra in a unique concert setting as it trades the traditional concert hall for a downtown parking garage.

🎸 October 3 – Windsor Beatlemania!
7:30 PM | Chrysler Theatre
Enjoy an evening celebrating the timeless music of The Beatles, with live performances of iconic hits from the Fab Four.

🎸 October 4 – Country Line Dance Night at Walkerville Brewery
6:00 PM | Walkerville Brewery
A high-energy country line dancing night with instruction from The Traveling Dancefloor, open dance floor, and the taproom bar open all evening.

🎷October 8–Whiskey Myers with Special Guest The Ransom Brothers
7:00 PM | The Colosseum at Caesars Windsor
Southern rock band Whiskey Myers will perform with The Ransom Brothers. The band, which emerged in 2007, is known for its genre-blending sound and extensive live-performance history.

Windsor’s comedy scene is bringing nonstop laughs with stand-up showcases, lighting up intimate venues all across the city.

😂 October 1 –Bert Kreischer – Permission to Party World Tour
8:00 PM | The Colosseum at Caesars Windsor
Comedian Bert Kreischer is scheduled to perform his Permission to Party World Tour at The Colosseum at Caesars Windsor.

😂 October 2 – Girl Night on Tour! All-Women LIVE Comedy
8:00 PM | The Tipsy Toucan
Windsor Laughs presents an evening of live stand-up comedy featuring an all-women lineup of comedians from across Ontario.

🎤 October 3 – Canadian Famous Comedy Tour LIVE
8:00 PM | The Tipsy Toucan
Windsor Laughs presents the Canadian Famous Comedy Tour, featuring Canadian comedy talent and live entertainment.

🎭 October 6 – Phogheads Comedy Showcase
See event details | Phog Lounge
A free weekly comedy showcase featuring local and touring comedians performing stand-up sets in Windsor.

✈️ October 1 – National Seniors Day at the Canadian Aviation Museum
See event details | Canadian Aviation Museum
Celebrate National Seniors Day with special tours, presentations, trivia, coffee and treats, door prizes, and more.

🍺 October 2–3 – Heimat Oktoberfest
See event details | Heimat Biergarten & Restaurant
Oktoberfest celebration featuring German food, Bavarian entertainment, competitions, trivia games, and live event programming.

👑 October 3 – The Princess Gala presented by Princess Party Sisters
2:00 PM – 4:00 PM | Polish Club Windsor
Enjoy an enchanting afternoon of royal fun with favourite princesses, live performances, and a festive princess dance party. This family-friendly celebration offers music, dancing, and plenty of magical moments for young guests to enjoy.

🍺 October 3 – Cookie Bar’s 3rd Annual Oktober Fest
See event details | Cookie Bar
Cookie Bar’s Oktoberfest-themed event features German-inspired festivities and seasonal entertainment.

🪄 October 3 – Potterfest
5:00 PM | Film Camp for Kids & Youth
Step into a magical evening at Windsor Potterfest, a family-friendly and affordable celebration designed for all ages, with activities especially suited to post-secondary students, preteens, and teens.

🥧 October 4 – Tart & Soul Butter Tart Festival
11:00 AM | WindsorEats
Enjoy a day of sweet treats, local food, and community fun at the Tart & Soul Butter Tart Festival. Sample a variety of delicious butter tarts from talented “Tartisans,” explore local food and makers, and cast your vote for your favourite in the People’s Choice Award.

👗 October 4 – RAW Evolution: Fashion Show + Pop-Up Event
6:00 PM – 9:00 PM | Water’s Edge Event Space
Experience RAW EVOLUTION, an evening celebrating creativity, self-expression, and emerging talent in Windsor’s fashion and arts community. Enjoy a live runway fashion show featuring emerging designers, explore a curated local vendor market, connect with creative entrepreneurs and artists, and take part in interactive photo moments and event activations.

Enjoy markets, shows, fashion at Windsor.

🌱 October 3 – 4th Annual YQGgreen Expo
9:00 AM | WFCU Centre
Discover a full day of sustainability, innovation, education, and community connection at the 4th Annual YQGgreen Expo. Presented

🛍️ October 3 – Lakeside Market
8:00 AM – 1:00 PM | 927 St. Joachim L’Association
Presented by Lakeside Home Solutions, the Lakeside Market brings together local farmers, growers, makers, artisans, small businesses, food vendors, and community organizations in a vibrant market atmospher

🧟 October 3 – Windsor Zombie Walk and Parade 2026
5:00 PM | Ouellette Avenue & Elliott Street
The dead are taking over Downtown Windsor! Join the Windsor Zombie Walk and Parade for a free, family-friendly evening featuring zombie contests, an undead parade, and plenty of Halloween fun.

🏎️ October 3 – Town of Essex Soapbox Derby & Family Picnic
7:00 AM | Town of Essex
Enjoy a fun-filled community day at the Town of Essex Soapbox Derby & Family Picnic. This family-friendly event brings the community together for an exciting soapbox derby and a relaxed picnic

📚 October 3 – Giant Book Sale – St. Matthew's Church
See event details | St. Matthew's Church
Browse through 10,000 neatly sorted books, CDs, and DVDs at the Giant Book Sale. With a huge selection of titles and media to explore, it’s a great opportunity to discover new favourites and hidden gems

🥕 October 3 – Downtown Windsor Farmers’ Market
See event details | Downtown Windsor
Spend your Saturday shopping local at the Downtown Windsor Farmers’ Market, where you’ll find farm-fresh fruits, vegetables, produce, and unique artisan food products showcasing some of the best offerings from the local area.

🍂 October 4 – Fall Market On The Farm at Bouchard Gardens
10:00 AM – 2:00 PM | Bouchard Gardens
Get ready for fall at the Fall Market On The Farm at Bouchard Gardens! Shop from local vendors and stock up on seasonal favourites, including fall home décor, pumpkins and gourds, colourful mums, fresh produce, baked goods, and much more.

🍂 October 4 – Fall Market
10:00 AM – 4:00 PM | LaSalle Event Centre
Celebrate the season at the Fall Market, featuring local vendors, seasonal finds, and food from Little Foot Foods’ Pierogi Stop.

🥕 October 4 – Sunday Farmers Market
See event details | WindsorEats Food Hall
Shop local at the Sunday Farmers Market at WindsorEats Food Hall, a monthly community market created as a place to discover local products, enjoy good food, and spend time together.

🪵 October 6 – Epoxy Resin Workshops – Side Table
See event details | Resin by Jenny
Create your own beautiful resin side table in this hands-on, beginner-friendly workshop. Choose your colours and design a unique piece using epoxy resin

🌸 October 7 – Fall Sip and Snip – Floral Arrangement Workshop
See event details | Vivace Estate Winery
The fourth Sip and Snip workshop of 2026 features a fall-themed floral arrangement activity, giving participants an opportunity to create a seasonal floral design.

🎨 October 8 – Dot Painting Workshop – Glow in the Dark Cosmic Moon
See event details | Beerded Dog Brewing Company
Get creative with a guided mandala dot-painting workshop where you’ll create your own glow-in-the-dark cosmic moon piece.

👻 October 8 – Mixed-Media Ghost Craft
4:30 PM | Windsor Public Library – Central Branch
Get creative this spooky season with an easy, all-ages mixed-media ghost craft at the Central Branch.

🍂 October 8– Autumn in the Vineyard
6:30 PM | Paglione Estate Winery, Harrow
A cozy autumn evening of wine, food and creativity — an intimate charcuterie masterclass & wine pairing with Thanksgiving-inspired styling tips.

Enjoy games, trivia and dinner nights in Windsor.

🎉 October 1-October 8 – Trivia Night
7:00 PM | The Manchester Bar
Weekly trivia night at The Manchester Bar in downtown Windsor, testing your knowledge for prizes and bragging rights.

🥃 October 2–4 – J.P. Wiser’s Whisky Weekend
See event details | J.P. Wiser’s Distillery Experience
A multi-day whisky event at the historic Hiram Walker Distillery in Windsor, featuring a kickoff Masterclass.

🍽️ October 3 – BBQ Steak Dinner at Bedford United Church
5:00 PM – 7:00 PM | Bedford United Church
Enjoy a community BBQ steak dinner featuring a baked potato with butter and sour cream, vegetables, salad, fresh rolls and butter, dessert, coffee, tea, and juice.

🎭 October 3 – Murder at the Masquerade
6:00 PM | Royal Canadian Legion Branch 644
Step into an evening of mystery and intrigue at Murder at the Masquerade. Doors open at 6:00 PM, with dinner served at 7:00 PM.

🎃 October 3 – The Boonies Halloween Bash
4:00 PM | The Boonies Drive-In Theatre
Get ready for a spooky evening of movies, costumes, candy, trucks, vendors, and family fun under the stars at The Boonies Halloween Bash! This

🍝 October 7 – Caboto Club Charity Pasta Night
4:00 PM | Giovanni Caboto Club
Enjoy a community Charity Pasta Night hosted by the Optimist Club of South Windsor.

🥃 October 8 – Kingsville Sip & Savour Speak Easy
4:00 PM | Banded Goose Brewing Co. 15 Main Street East Kingsville, Ontario
Step back into the 1920s for an evening of secret sips, great bites, and good company in downtown Kingsville.

🎲 October 7 – Game Nights @ Central Library for Kids!
6:00 PM | Central Library, Downtown Windsor
Enjoy a free kids’ game night at the Central Library in downtown Windsor, featuring board games and fun activities for children.

Enjoy the sports events in Windsor of your choice!

🏒 October 1 – North Bay Battalion vs. Windsor Spitfires – First Responders
See event details | WFCU Centre
Honour those who answer the call during First Responders Night, as the Windsor Spitfires recognize the dedicated first responders who serve the community.

🥌 October 1 – October 4 – PLAY FOR FREE! Free Learn to Curl
See event details | Capri Pizzeria Recreation Complex
Try something new with free Learn to Curl sessions as part of Windsor’s Staycation Activation program.

🏈 October 3 – Windsor Lancers Football
7:00 PM | Alumni Stadium, University of Windsor
Catch the Windsor Lancers in action on Alumni Weekend as they take on York at Alumni Stadium.

🎳 October 3 – Forest Glade Optimist Junior Bowling
See event details | SuperBowl Lanes
Introduce children to the fun of bowling through the Forest Glade Optimist Junior Bowling League.

🏃October 5 – United Way’s Fourth Annual Charity Golf Tournament
10:00 AM | Beach Grove Golf & Country Club
Join us for United Way’s 4th Annual Charity Golf Tournament and tee off for a great cause while helping build stronger, brighter communities across our region.

That's your week across Windsor-Essex. Whether you're catching UB40 or Whiskey Myers at Caesars, dancing at Oktoberfest, or joining the undead for the Zombie Walk downtown, there's plenty to keep the fall spirit alive. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse