Windsor, October's almost here and the calendar is still going strong. This week (Sep 24–Oct 1) Bert Kreischer brings his Permission to Party World Tour to The Colosseum at Caesars, the Windsor Symphony Orchestra opens its new season with From Paris to Madrid, and the 47th Ruthven Apple Festival kicks off fall right. Add the Windsor Essex Night Market Hop, live theatre, and 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.

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.

🎶 September 26 – ABBA Revisited – Windsor
8:00 PM | Chrysler Theatre, St. Clair College Centre for the Arts
Get ready to sing along as ABBA Revisited brings the music of ABBA to Windsor for an exciting night of live entertainment.

🎻 September 26–27 – Opening Weekend: From Paris to Madrid
7:30 PM Saturday & 2:30 PM Sunday | Capitol Theatre
The Windsor Symphony Orchestra opens its new season with From Paris to Madrid, a vibrant concert experience celebrating the music and spirit of two iconic European cities.

🎶 September 28 – Relive the Music: 50s, 60s, and 70s Show
7:30 PM | The Capitol Theatre
Take a musical journey through the 50s, 60s, and 70s with Relive the Music, featuring beloved hits from three unforgettable decades. This expanded show adds the biggest sounds of 70s rock, disco, and funk

🎭 October 1 – OnStage: CBC’s Tom Allen: A Poe Cabaret
See event details | 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.

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

😂 September 26 – James Cummins LIVE Comedy
8:00 PM | The Tipsy Toucan
James Cummins left his life as a truck driver and strip club DJ in 2017 to pursue standup comedy!

😂 September 26 – Standup Comedy at Sidelines Sports Bar & Grill!
8:00 PM | Sidelines Sports Bar & Grill
Come join us for THE LONGEST RUNNING MONTHLY COMEDY SHOW IN WINDSOR. Standup Comedy at Sidelines Sports Bar & Grill!

🎭 September 29 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Downtown Windsor
Enjoy a weekly stand-up comedy showcase featuring a rotating mix of local and touring comics in downtown Windsor.

🤣 October 1 – Bert Kreischer Permission to Party World Tour
8:00 PM | The Colosseum at Caesars Windsor
The hilarious Bert Kreischer is hitting Caesars Windsor with his Permission to Party World Tour, live from The Colosseum stage on Thursday, October 1 at 8 PM.

🍎 September 26–27 – 47th Ruthven Apple Festival
See event details | Colasanti's Tropical Gardens
Celebrate apples, community, and classic fall traditions at the 47th Ruthven Apple Festival, a beloved annual Essex County celebration. Enjoy the festive atmosphere and discover a wonderful way to welcome the autumn season with family and friends.

🎉 September 24-26 – Heimat Oktoberfest
Heimat Biergarten & Restaurant
Experience Oktoberfest with our 1L bier steins filled with Paulaner Oktoberfest beer, authentic German food, Bavarian dancers, fun competitions/trivia games throughout the night and the legendary Hype Man Steve.

🚆 September 24–27 – National Rail Safety Week
8:30 AM | Tecumseh
Take part in National Rail Safety Week, a community awareness initiative focused on promoting safe practices around railway tracks, crossings, and rail property.

🎓 September 29 – Practical Nursing Dinner & Pinning Ceremony Class of 2026
Doors 5:00 PM, Dinner 6:00 PM | Chrysler Theatre
Celebrate the Practical Nursing Class of 2026 at a special dinner and pinning ceremony recognizing the accomplishments and dedication of graduating nursing students. The evening brings classmates, faculty, friends, and family together for a meaningful celebration of this important milestone

Enjoy markets, shows, fashion at Windsor.

🎭 September 24–26 – All My Sons at Kordazone Theatre
See event details | Kordazone Theatre
Experience Arthur Miller’s powerful drama All My Sons, his first major Broadway success. First presented in 1947, the play won both the New York Drama Critics’ Circle Award for Best New Play and the Tony Award® for Best Author

🌙 September 24–27 – Windsor Essex Night Market Hop
See event details | Various Locations, Windsor-Essex
Markets. Music. Makers. Memories. Explore Windsor-Essex after dark during the Windsor Essex Night Market Hop, an invitation to discover local districts and neighbourhoods while shopping, supporting local businesses, and connecting with the community.

🎭 September 25–27 – BRC Theatre Co. Presents Mean Girls
See event details | Sho Art, Spirit & Performance
BRC Theatre Co. proudly presents Mean Girls, the hit musical based on the iconic Paramount Pictures film.

🎟️ September 25–27 – Death of a Salesman at the Bank Theatre
See event details | The Bank Theatre
Experience Arthur Miller’s acclaimed tragedy Death of a Salesman, a powerful story centered on Willy Loman and his struggles with family, work, expectations, and the pursuit of success.

🥕 September 26 – 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.

🛍️ September 26 – 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 atmosphere.

🌱 September 26 – LaSalle Horticultural Society Fall Plant Sale
9:00 AM | LaSalle
Discover a variety of plants and seasonal gardening finds at the LaSalle Horticultural Society Fall Plant Sale.

🎨 September 27 – Palette Play: Pumpkin Painting
See event details | Leamington Arts Centre
Let creativity take centre stage with the first class in the Palette Play series. Designed for children ages 8 to 12, this hands-on art experience gives young artists the opportunity to explore their creativity

🎨 September 27 : Wine Glass Paint & Sip
12:00 PM to 3:00 PM | Cooper’s Hawk Vineyards
Our September Sunflowers Wine Glass Sip & Paint Afternoon is officially open for registration! Join us for a fun and relaxing creative experience at the beautiful Cooper’s Hawk Vineyards.

🛍️ September 27 – Lakewood Mini Market
See event details | Lakewood Park
Shop Local. Support Community. Spend your Sunday exploring the Lakewood Mini Market, held on the Plaza on the second and fourth Sunday of each month through September

🌙 September 27 – LaSalle Night Market
4:00 PM | LaSalle
Explore the LaSalle Night Market, a community event offering an opportunity to discover local vendors, unique finds, and seasonal offerings while enjoying an evening atmosphere in LaSalle.

Enjoy games, trivia and dinner nights in Windsor.

⛳ September 24 – Mayor's Spotlight on Business Golf and Dinner
11:00 AM | Kingsville
Join the community for the Mayor's Spotlight on Business Golf and Dinner, a special event featured on the Town of Kingsville’s festivals and events calendar.

🌙 September 25th – Walkerville Distillery District Night Market
5:00 PM | Walkerville Brewery
Join us at the Walkerville Distillery District Night Market on Friday, June 26th from 5pm-11pm!

🚢 September 26 – Cruise for a Cause
6:00 PM | Windsor Premier Cruises
Spend an evening on the Detroit River while supporting The Windsor Residence for Young Men (WRYM) at Cruise for a Cause, a sunset cruise fundraiser bringing the community together for a meaningful cause.

🎃 September 26 – 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!

👻 September 26 – Haunted History of the Navy Yard
7:00 PM | King's Navy Yard, Amherstburg
Explore the fascinating and spooky side of local history on a walking tour through the haunted history of the Navy Yard, led by local historian and actor Rob Tymec.

🍇 September 27- The Hospice Wine Tour
11:30 AM | Ciociaro Club of Windsor
Join us on Sunday, September 27, 2026 for a fun-filled day of touring local wineries, all in support of The Hospice of Windsor and Essex County!

🎲 September 30 – Game Nights @ Central Library for Kids!
6:00 PM – 8:00 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!

🎳 September 26 – 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. Young participants can learn bowling skills, meet new friends, build confidence, and enjoy an active and welcoming experience on the lanes

🥌 September 26 – 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

🏒 September 26 – Game On! Beyond the Ice with Gilbert Dionne & Friends
8:00 PM | Club 9 Banquet Hall
A special evening combining hockey, comedy, and music, featuring Gilbert Dionne and friends.

💪 September 26 – Windsor-Essex Fitness Expo
See event details | Event Centre at LaSalle Landing
Kickstart your fall fitness goals at the Windsor-Essex Fitness Expo, featuring 50+ vendors, live demonstrations, competitions, and more.

🏃 September 27 – motionball Marathon of Sport Windsor 2026
9:00 AM | University of Windsor
Join the community for motionball Marathon of Sport Windsor 2026, a sporting event supporting the Special Olympics Canada Foundation.

That's your week across Windsor-Essex. Whether you're catching Bert Kreischer at Caesars, apple picking at the Ruthven Apple Festival, or exploring the Night Market Hop after dark, there's plenty to keep the fall spirit going. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse