What's Happening: Windsor

Free Admission at Chimczuk Museum and Art Windsor-Essex Orange Shirt Day

Date: Wednesday, September 30
Time: 10:00 am
Location: Chimczuk Museum
Summary: Explore local Indigenous history and culture with free admission to the Chimczuk Museum and Art Windsor Essex on the National Day for Truth and Reconciliation.

Kingsville – National Day for Truth and Reconciliation

Date: Wednesday, September 30
Time: 11:00 am
Location: Jasperson Lane
Summary: Come together as a community to commemorate the survivors and victims of residential schools, their families and communities

Twilight Paint & Trivia Night

Date: Wednesday, September 30
Time: 6:30 pm – 8:30 pm
Location: Windsor Craft Club
Summary: Twilight Fans — start your hoa, hoa, hoa season off right at Windsor Craft Club!

National Seniors Day at the Canadian Aviation Museum

Date: Thursday, October 01
Time: 11:00 am
Location: Canadian Aviation Museum
Tickets: $5.00 – $55
Summary: Come spend the day with us as we celebrate the experiences, knowledge and contributions of our seniors. Special tours, presentations. trivia, coffee and treats, door prizes and more.

Fall Convocation - Chatham

Date: Thursday, October 01
Time: 1:00 pm – 9:00 pm
Location: St. Clair College
Summary: Join us in celebrating the Fall 2026 Convocation Ceremonies in Chatham. Click for more details.

Encore Productions Presents: Whisky, Water and Wild Times

Date: Thursday, October 01
Time: 6:00 pm
Location: Essex County Library – Toldo Branch
Summary: Step back into the Roaring Twenties, when Prohibition transformed the Detroit River into one of the busiest smuggling routes of the era.

Leamington Comic Jam

Date: Thursday, October 01
Time: 6:00 pm
Location: Leamington Arts Centre
Tickets: Free
Summary: Join us at the LAC for our monthly comic jam, happening the first Thursday of every month from 6-8pm!

North Bay Battalion V.S. Windsor Spitfires – First Responders

Date: Thursday, October 01
Time: 7:05 pm
Location: WFCU Centre
Summary: Honouring those who answer the call. Head on out to the WFCU Centre, for an exciting OHL Matchup as the Spitfires matchup against one of their rivals the North Bay Battalion!

OnStage: CBC’s Tom Allen: A Poe Cabaret SOLD OUT

Date: Thursday, October 01
Time: 7:30 pm
Location: Capitol Theatre
Summary: Step onto the stage for an immersive concert experience featuring live narration, haunting orchestral works, and atmospheric storytelling inspired by the mysterious world of Edgar Allan Poe.

Bert Kreischer Permission to Party World Tour

Date: Thursday, October 01
Time: 8:00 pm
Location: The Colosseum at Caesars Windsor
Summary: The hilarious Bert Kreischer is hitting Caesars Windsor with his Permission to Party World Tour, live from The Colosseum stage

Café Concert: CBC’s Tom Allen: A Poe Cabaret SOLD OUT

Date: Friday, October 02
Time: 11:00 am
Location: Capitol Theatre
Summary: Enjoy coffee, conversation, and live orchestral music from the stage as this immersive Café Series concert brings the mystery and atmosphere of Edgar Allan Poe to life through music and narration.

Heimat Oktoberfest

Date: Friday, October 02 – Saturday, October 03
Time: 5:00 pm
Location: Heimat
Summary: Experience Oktoberfest at Heimat

Create And Paint Your Own Doormat

Date: Friday, October 02 – Saturday, October 03
Time: 6:30 pm – 8:30 pm
Location: 1009 Drouillard Rd #2
Tickets: $65.00
Summary: Join us at Windsor Craft Club to create a custom door welcome mat for your home.

Monarch Cafe Series – Songs and Stories in the Round

Date: Friday, October 02
Time: 6:30 pm
Location: The Bank Theatre
Summary: Join us at the Bank Theatre for Songs and Stories in the Round. The series is similar to the popular Nashville Bluebird Cafe-style with all genres, with Justin Latam as the artist in residence + 3 local or touring musicians.

J.P. Wiser’s Whisky Weekend

Date: Friday, October 02 – Sunday, October 04
Time: 7:00 pm
Location: J.P. Wiser’s Distillery Experience
Summary: A celebration featuring whisky tastings, distillery tours, live music, cocktails, and more.

• Sat - 11:00 am
• Sun - 11:00 pm

The Australian Bee Gees Show - A Tribute To The Bee Gees

Date: Friday, October 02
Time: 7:30 pm
Location: Chrysler Theatre
Tickets: Mainfloor: $53.75 + taxes & fees Boxes: $63.75 + taxes & fees
Summary: Paquette Entertainment Company Presents:

The Pet by Shane Devon Nelson

Date: Friday, October 02 – Saturday, October 03
Time: 8:00 pm
Location: Shadowbox Theatre
Summary: Experience a brand new work of psychological horror this spooky season with ‘The Pet’ by Shane Devon Nelson, only at The Shadowbox Theatre!

UB40 at Caesars Windsor

Date: Friday, October 02
Time: 8:00 pm
Location: The Colosseum at Caesars Windsor
Summary: Be there when UB40 hits The Colosseum stage on Friday, October 2 at 8 PM.

First Robotics Canada Girls And Allies Youth Summit - Windsor

Date: Saturday, October 03
Time: 8:00 am – 4:30 pm
Location: St. Clair College of Applied Arts and Technology
Tickets: Free
Summary: Join us on Oct. 3 in Windsor for the free FIRST Robotics Canada Girls & Allies Youth Summit! Grades 8–12 welcome. Registration required.

Lakeside Market

Date: Saturday, October 03
Time: 8:00 am
Location: 927 St Joachim L’Association
Summary: Don’t miss the Lakeside Market!

Ojibway Nature Centre 50 Year Celebration

Date: Saturday, October 03
Time: 11:00 am
Location: Ojibway Nature Centre
Summary: Everyone is invited to stop by the nature centre to enjoy some special exhibits showcasing timeless moments in the history of this cherished landmark.

Whisky Weekend - October 3rd, 2026

Date: Saturday, October 03 – Sunday, October 04
Time: 11:00 am – 8:00 pm
Location: J.P. Wiser's Experience
Tickets: $10.00 – $125.00
Summary: Join us at J.P. Wiser’s Whisky Weekend! Experience distillery tours, exclusive masterclasses, tasting flights, live music, and food trucks.

Cookie Bar’s 3rd Annual Oktober Fest

Date: Saturday, October 03
Time: 12:00 pm
Location: Cookie Bar
Summary: Break out the lederhosen and stretch those beer-holding arms we’re bringing back our rowdiest tradition for round two.

Kids Monthly Art Classes, Drawing, Painting, Clay, Mixed Media (Ages 6–13)

Date: Saturday, October 03
Time: 1:00 pm – 3:00 pm
Location: Expressive Brush Art Studio
Tickets: $55.00 – $345.00
Summary: Join our fun Saturday art classes! Spark your child’s creativity and build confidence through hands-on projects designed for young artists

Art Windsor Essex Guided Tour

Date: Saturday, October 03
Time: 2:00 pm
Location: Art Windsor Essex
Summary: Discover the stories behind the artworks at Art Windsor–Essex!

Taco Mania

Date: Saturday, October 03
Time: 2:00 pm
Location: Windsor Eats
Summary: Tailgate Takeout and WindsorEats are teaming up to present the inaugural TacoMania: an all-out taco showdown

The Princess Gala presented by Princess Party Sisters

Date: Saturday, October 03
Time: 2:00 pm
Location: Polish Club Windsor
Summary: Join the fun at The Princess Gala, hosted by Princess Party Sisters—a magical day of sparkle and smiles!

Canada Classical By Candlelight | Glenwood United Church | Windsor

Date: Saturday, October 03
Time: 5:00 pm – 6:00 pm
Location: Glenwood United Church
Tickets: $17.54 – $55.09
Summary: Experience the anthems of Canada’s finest acts, performed live by a string quartet in an intimate candlelight setting.

FREE Concert: Classical in the Concrete

Date: Saturday, October 03
Time: 6:00 pm
Location: Pelissier Street Parking Garage
Tickets: Free
Summary: We’re trading the concert hall for a parking garage!

Rocktober with Strike Tyson Cruise

Date: Saturday, October 03
Time: 6:30 pm
Location: Windsor Premier Cruises
Summary: Get ready to make waves on the Macassa Bay boat for Rocktober with Strike Tyson.

Abba Vs Queen By Candlelight | Glenwood United Church | Windsor

Date: Saturday, October 03 – Sunday, October 04
Time: 7:00 pm – 8:00 pm
Location: Glenwood United Church
Tickets: $17.54 – $59.79
Summary: Experience the greatest hits from ABBA & Queen, performed live by a string quartet in an intimate candlelight setting.

Windsor Lancers Football

Date: Saturday, October 03
Time: 7:00 pm
Location: University of Windsor – Alumni Stadium
Summary: Catch the Windsor Lancers in action on Alumni Weekend as they take on York at Alumni Stadium.

Windsor Beatlemania!

Date: Saturday, October 03
Time: 7:30 pm
Location: Chrysler Theatre
Tickets: $52.50+taxes & fees
Summary: Ice Capp Productions Presents:

Puppy Love's Howlween Party

Date: Saturday, October 03
Time: 8:00 pm – 10:00 pm
Location: Villains
Tickets: $10.00
Summary: Join some of Windsor's finest drag performers for a fangtastic Halloween drag show & dance party!

Sweet Beats – 30th Anniversary featuring Terrence Parker

Date: Saturday, October 03
Time: 10:00 pm
Location: Erie St GastroPub
Summary: Celebrate 30 years of Sweet Beats with DJ Terrence Parker. Truly, one of the best live DJ performers from Detroit. Get ready Windsor!

Harvest & Flow at Wagner Orchards

Date: Sunday, October 04
Time: 9:00 am
Location: Wagner Orchards & Estate Winery
Summary: Club Pilates & Wagner Orchards welcome you for another great event!

Fall Market

Date: Sunday, October 04
Time: 10:00 am – 4:00 pm
Location: Event Centre at LaSalle Landing
Summary: Join us on October 4, 2026, from 10:00 a.m. to 4:00 p.m. at the LaSalle Event Centre (970 Front Rd., LaSalle) for a fun-filled Fall Market featuring over 100 local vendors.

Fall Market On The Farm at Bouchard Gardens

Date: Sunday, October 04
Time: 10:00 am – 4:00 pm
Location: Bouchard Gardens
Summary: Get ready for the Fall and load up on all your Fall decor/needs from local vendors!

Sunday Farmers Market

Date: Sunday, October 04
Time: 11:00 am
Location: WindsorEats Food Hall
Summary: This isn’t a grab-and-go parking lot market. It’s designed for people to browse, snack, sip, and stay awhile.

Whisky Weekend - October 4th, 2026

Date: Sunday, October 04
Time: 11:00 am – 5:00 pm
Location: J.P. Wiser's Experience
Tickets: $10.00 – $125.00
Summary: Join us at J.P. Wiser’s Whisky Weekend! Experience distillery tours, exclusive masterclasses, tasting flights, live music, and food trucks.

Windsor Lancers Soccer

Date: Sunday, October 04
Time: 1:00 pm
Location: University of Windsor – Alumni Stadium
Summary: Catch the Windsor Lancers in action on Alumni Weekend as they take on Brock at Alumni Stadium.

Playwriting 2: Creating Memorable Scenes

Date: Sunday, October 04
Time: 2:30 pm – 5:30 pm
Location: The Shadowbox Theatre
Tickets: $135.00
Summary: Playwriting 2: Creating Memorable Scenes - a six(6) week course offered as part of the 2026 Theatre Skills Education Program

Country Line Dance At Walkerville Brewery

Date: Sunday, October 04 – Monday, October 05
Time: 6:00 pm – 9:00 pm
Location: Walkerville Brewery
Tickets: $10.00
Summary: Join us for a high-energy Country Line Dancing Night filled with great music, easy-to-follow steps, and one heck of a good time!

Raw Evolution: Fashion Show + Pop-Up Event

Date: Sunday, October 04 – Monday, October 05
Time: 6:00 pm – 9:00 pm
Location: 2879 Riverside Dr E
Tickets: $10.00 – $40.00
Summary: RAW EVOLUTION is more than a fashion show—it's a celebration of creativity, self-expression, and the next generation of talent.

Canadian Famous Comedy Tour Live At The Tipsy Toucan (Oct 3rd)

Date: Sunday, October 04
Time: 8:00 pm – 9:30 pm
Location: The Tipsy Toucan
Tickets: $25.00
Summary: Canadian Famous Comedy Tour at The Tipsy Toucan-One night of top Canadian standup featuring Braydon Lynch and headliner Tyler Morrison

Sweet Beats - 30th Anniversary Featuring Terrence Parker

Date: Sunday, October 04
Time: 10:00 pm – 2:30 am
Location: 839 Erie St E
Tickets: $20.00 – $30.00
Summary: Celebrate 30 years of Sweet Beats with DJ Terrence Parker. Truly, one of the best live DJ performers from Detroit. Get ready Windsor!

Food Handler Certification Exam - Masonic Temple, Windsor

Date: Tuesday, October 06
Time: 10:30 am – 11:30 am
Location: Masonic Temple Ballroom
Tickets: $10.00
Summary: This registration is for the Windsor-Essex County Health Unit's Food Handler Certification Exam held in Windsor at the Masonic Temple.

Epoxy Resin Workshops-Side Table

Date: Tuesday, October 06
Time: 6:00 pm
Location: Resin by Jenny
Tickets: $105.00
Summary: Create your own beautiful resin side table in this hands-on beginner-friendly workshop!

Parent Information Night

Date: Tuesday, October 06
Time: 6:00 pm – 8:00 pm
Location: St. Clair College
Summary: Do you have questions about attending St. Clair College? Do your parents have specific questions about the program you've selected?

Windsor - Opp Women's Focused Shuttle Run And Information Session

Date: Tuesday, October 06 – Wednesday, October 07
Time: 6:00 pm – 9:00 pm
Location: St. Clair College of Applied Arts and Technology
Tickets: Free
Summary: The OPP is pleased to invite you to attend and try the 20m Leger Shuttle Run!

Stencil Paint Workshop

Date: Tuesday, October 06
Time: 6:30 pm
Location: Daisy & Co. Wine Bar
Summary: Relax and get creative with local artist Annie Froese! Enjoy an evening of stencil painting, creativity and fun at Daisy & Co.

Italian Culture Lecture Series – Italian Citizenship Seminar

Date: Tuesday, October 06
Time: 7:00 pm
Location: Giovanni Caboto Club
Summary: You are invited to join us every Tuesday evening in October, plus Tuesday, November 3, for an informative and entertaining series featuring five knowledgeable guest speakers. Tuesday, October 6 — Italian Citizenship Seminar presented by Andreea Brinza

Phogheads Comedy Showcase

Date: Tuesday, October 06
Time: 8:30 pm
Location: None
Summary: Join us at Phog Lounge for a FREE weekly comedy showcase featuring some of the funniest local and touring comedians performing fresh stand-up sets in one of the city’s most intimate venues.