What's Happening: Windsor

Seniors Program: Guided Tour and Watercolour Workshop with Sandra Ellis

Date: Wednesday, October 14
Time: 10:30 am
Location: Art Windsor Essex
Summary: Artist-educator Sandra Ellis will show us how to create watercolour painting inspired by the exhibition!

Wednesday Wisdom Networking Event

Date: Wednesday, October 14
Time: 5:00 pm – 7:00 pm
Location: Madame Monsieur
Tickets: $10.00
Summary: "Big things start with small connections, come spark one with us" - Frank Abbruzzese

Kingsville Migration Festival

Date: Thursday, October 15 – Sunday, October 18
Time: 10:00 am
Location: Town of Kingsville
Summary: Kingsville welcomes the community to a celebration of migration, heritage, nature conservation and Jack Miner.

Dueling Pianos Soiree: Live Music By Request, Dinner, and Dancing

Date: Thursday, October 15
Time: 6:00 pm
Location: Giovanni Caboto Club
Tickets: $125
Summary:

Do you make a delicious homemade salami, capicollo, prosciutto, or lonzo? Now is your chance to put your skills to the test!

Join us for our Gara di Salumi, a friendly competition celebrating the Italian tradition of homemade cured meats. Bring your best creation and let our judges taste and evaluate your entry.

Encore Productions Presents: Whisky, Water and Wild Times

Date: Thursday, October 15
Time: 6:00 pm
Location: Essex County Library – Essex Branch
Summary: Step back into the Roaring Twenties, when Prohibition transformed the Detroit River into one of the busiest smuggling routes of the era.

Mystery Mural Project Paint Night

Date: Thursday, October 15
Time: 6:00 pm
Location: The Bank Theatre
Summary: Join us for the Mystery Mural Project Paint Night! Your task is simple: recreate the image provided as best you can using the supplies in your kit. The magic happens when we bring all of the pieces together. Much like community theatre, this mural is something that can only be created when everyone plays their part.

Dueling Pianos At Walkerville Brewery

Date: Thursday, October 15 – Friday, October 16
Time: 7:00 pm – 10:00 pm
Location: Walkerville Brewery
Tickets: $15.00
Summary: Join us on Thursday, October 15th at Walkerville Brewery for Rose City Dueling Pianos ft. Marc Dorian & Jeremy Coulter

Sudbury Wolves V.S. Windsor Spitfires – The Great Outdoors

Date: Thursday, October 15
Time: 7:05 pm
Location: WFCU Centre
Summary: Come celebrate the 4th annual great outdoors night! Head on out to the WFCU Centre, for an exciting OHL Matchup as the Spitfires matchup against one of their rivals the Sudbury Wolves!

Menopause The Musical

Date: Thursday, October 15
Time: 7:30 pm
Location: Chrysler Theatre
Tickets: $60+ taxes & fees $80+ taxes & fees (Box Seats & Rows A-C)
Summary: Shaggypup Productions Presents:

The Pet by Shane Devon Nelson

Date: Thursday, October 15 – Saturday, October 17
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!

Detroit Free Press Marathon

Date: Friday, October 16 – Sunday, October 18
Time: 7:00 am
Location: None
Summary: Check out the Detroit Free Press Marathon!

OHL Battle of the Border

Date: Friday, October 16 – Sunday, October 18
Time: 9:00 am
Location: THE WFCU CENTRE
Summary: Don’t miss OHL Battle of the Border!

Chalk Pastel Country Landscape Class For Adults And Teens

Date: Friday, October 16
Time: 5:00 pm – 6:30 pm
Location: Expressive Brush Art Studio
Tickets: $30.00
Summary: Create a peaceful country landscape with chalk pastels while learning blending, layering, & texture techniques in a beginner-friendly class

Kingsville Migration Festival

Date: Friday, October 16 – Sunday, October 18
Time: 6:00 pm
Location: Town of Kingsville
Summary: Kingsville welcomes the community to a celebration of migration, heritage, nature conservation and Jack Miner.

Windsor Singles, Stand Up Comedy And Matchmaking

Date: Friday, October 16 – Saturday, October 17
Time: 7:00 pm – 9:00 pm
Location: 138 University Ave W
Tickets: $5.00 – $20.00
Summary: “Laugh. Mingle. Maybe Match.”

Owen Sound Attack V.S. Windsor Spitfires – Fight Night

Date: Friday, October 16
Time: 7:05 pm
Location: WFCU Centre
Summary: It is going to be a physical one! Head on out to the WFCU Centre, for an exciting OHL Matchup as the Spitfires matchup against one of their rivals the Owen Sound Attack!

Dear Evan Hansen – Arts Collective Theatre

Date: Friday, October 16 – Sunday, October 18
Time: 8:00 pm
Location: Capitol Theatre Windsor
Summary: Arts Collective Theatre is proud to present Dear Evan Hansen, a contemporary musical about connection, honesty, and what happens when one small moment changes everything.

Evil Dead: The Musical at Kordazone Theatre

Date: Friday, October 16 – Sunday, October 18
Time: 8:00 pm
Location: Kordazone Theatre
Summary: EVIL DEAD: THE MUSICAL takes all the elements of the cult classic films, The Evil Dead, Evil Dead 2, and Army of Darkness and combines them for one of the craziest, funniest, and bloodiest theatrical experiences of all time.

Menopause The Musical

Date: Friday, October 16
Time: 8:00 pm
Location: Chrysler Theatre
Tickets: $60+ taxes & fees $80+ taxes & fees (Box Seats & Rows A-C)
Summary: Shaggypup Productions Presents:

The Pet By Shane Devon Nelson

Date: Friday, October 16
Time: 8:00 pm – 10:00 pm
Location: The Shadowbox Theatre
Summary: Post Productions presents a new psychological stage horror and winner of the 2025 Windsor-Essex Playwriting Contest: The Pet by Shane Nelson

Family Fun Fall Market

Date: Saturday, October 17
Time: 10:00 am
Location: Event Centre at LaSalle Landing
Tickets: Free
Summary: Shop local from over 80+ unique local vendors!

Art at the Otentiks

Date: Saturday, October 17 – Sunday, October 18
Time: 11:00 am
Location: Point Pelee National Park
Tickets: FREE
Summary: Art at the oTENTiks is a two-day event featuring artists and artisans demonstrating their craft and selling their goods.

Duff-Bâby House – Open Days

Date: Saturday, October 17
Time: 12:00 pm
Location: Duff-Baby House
Summary: Following extensive restoration work by the Ontario Heritage Trust and the installation of new exhibits the Duff-Bâby House is ready to welcome visitors back

Notable Ancestors Who Have Left Their Mark On Windsor

Date: Saturday, October 17
Time: 1:30 pm – 2:30 pm
Location: Windsor Grove Cemetery
Tickets: $25.00
Summary: Tour historical Windsor Grove Cemetery and learn about individuals and families whose names are familiar to many Windsorites.

Ghost Ship Cruise

Date: Saturday, October 17
Time: 6:00 pm
Location: Windsor Premier Cruises
Summary: Join us for an early Halloween Cruise – A Sunset cruise with a spooky flare. DJ Chino will be mixing the beats to make this Ghost Ship event spooktacular!

Stand Up Comedy Show

Date: Saturday, October 17 – Sunday, October 18
Time: 7:00 pm – 9:00 pm
Location: Meteor
Tickets: $5.00 – $7.00
Summary: STAND UP COMEDY SHOW, 3 COMICS, ONE LEGENDARY NIGHT

Windsor Lancers Hockey

Date: Saturday, October 17
Time: 7:30 pm
Location: Adie Knox Herman Arena
Summary: Catch the Windsor Lancers in action as they take on Western at Adie Knox Herman Arena.

Ben Albert: Live in Windsor

Date: Saturday, October 17
Time: 8:00 pm
Location: The Tipsy Toucan
Summary: Headliner Ben Albert brings his wild night of big laughs to Windsor for some intimate shows. Come watch this rising star!

Diablerie Vampire Ball

Date: Saturday, October 17 – Sunday, October 18
Time: 8:00 pm
Location: Waters Edge Event Centre
Summary: Embrace The Night For one unforgettable night, mystery, elegance, and spectacle

Fleetwood Mac Mania

Date: Saturday, October 17
Time: 8:00 pm
Location: Chrysler Theatre
Tickets: $42.95+taxes & fees
Summary: Beach Towel Communication Presents:

Standup Comedy at Sidelines Sports Bar & Grill!

Date: Saturday, October 17
Time: 8:00 pm
Location: Sidelines Sports Bar & Grill
Tickets: $10 – $15
Summary: Get ready to laugh at Standup Comedy at Sidelines Sports Bar & Grill!

Detroit Free Press Marathon

Date: Sunday, October 18
Time: 7:00 am
Location: None
Summary: Check out the Detroit Free Press Marathon!

Line the Drive for the The Detroit Free Press International Marathon

Date: Sunday, October 18
Time: 7:00 am
Location: Riverside Drive, downtown
Summary: Check out the Detroit Free Press Marathon!

Tecumseh Farmers Market

Date: Sunday, October 18
Time: 9:00 am
Location: Lacasse Park
Summary: Discover fresh, locally grown produce, handmade goods, and unique treasures from our talented local vendors.

Race into the Harvest 5k

Date: Sunday, October 18
Time: 9:30 am
Location: Mastronardi Estate Winery
Summary: Get ready for a 5K unlike anything else! Join us at Mastronardi Estate Winery on Sunday, October 18, 2026, for Race Into the Harvest — a one-of-a-kind 5K obstacle course through the vineyard, combining running, fall fun, wine, and a great cause!

Fall Wellness Fair – Unity Spiritual Centre of Windsor

Date: Sunday, October 18
Time: 10:00 am
Location: Maryvale Children’s Mental Health Centre
Summary: Visit our wide variety of exhibitors, including wellness providers. Join in engaging workshops, including yoga, meditation and reiki, drumming circle and more. Vegan food, book sale, art gallery and thrift shop are all part of the day’s events!

Ford City Flea Market

Date: Sunday, October 18
Time: 10:00 am
Location: 1000 Block of Drouillard Road
Summary: Head on down to Ford City for the Ford City Flea Market!

Harvest and Horses

Date: Sunday, October 18
Time: 11:00 am
Location: John R. Park Homestead
Tickets: $6.00 – $30.00
Summary: Don’t miss this longstanding, family-favourite fall festival!

Perfect Pairing Wine & Food Tasting – Candy!

Date: Sunday, October 18
Time: 12:00 pm
Location: Cooper’s Hawk Vineyards
Summary: Join us for a guided tasting experience featuring a  selection of CHV wines, paired with delicious treats inspired by everyone’s favourite – candy!

The May Court Club – Book Lovers’ Luncheon & Silent Auction

Date: Sunday, October 18
Time: 12:00 pm
Location: The Windsor Club
Summary: This year’s edition of The Book Lovers’ Luncheon and Silent Auction features authors you would not want to miss!

Spooky Plant & Paint ✨

Date: Sunday, October 18
Time: 3:30 pm – 5:30 pm
Location: 1009 Drouillard Rd #2
Tickets: $25.00
Summary: Come join us at Windsor Craft Club for a plant and paint night. Choose a plant, paint your pot and finalize it with decorative pebbles.

Music Bingo Trivia at Walkerville Brewery

Date: Sunday, October 18
Time: 5:00 pm
Location: Walkerville Brewery
Summary: A night filled with a little bit of bingo, a little bit of trivia and a whole lot of music!

The Black Keys: PEACHES 'N KREAM at The Colosseum

Date: Sunday, October 18
Time: 7:30 pm
Location: The Colosseum at Caesars Windsor
Summary: The Colosseum welcomes The Black Keys!

Ben Albert: Live In Windsor

Date: Sunday, October 18
Time: 8:00 pm – 9:30 pm
Location: The Tipsy Toucan - Public House
Tickets: $19.00 – $24.00
Summary:

Headliner Ben Albert brings his wild night of big laughs to Windsor for some intimate shows. Come watch this rising star!

An additional show is at 10:00 pm

Diablerie Vampire Ball

Date: Sunday, October 18
Time: 8:00 pm – 2:00 am
Location: Water's Edge Event Centre
Tickets: $60.00 – $140.00
Summary: Embrace the night. Join us for an unforgettable night where mystery, glamour, and excitement intertwine in an immersive event like no other.

Standup Comedy At Sidelines Sports Bar & Grill!

Date: Sunday, October 18
Time: 8:00 pm – 9:30 pm
Location: Sidelines Sports Bar & Grill
Tickets: $10.00
Summary: Come join us for THE LONGEST RUNNING MONTHLY COMEDY SHOW IN WINDSOR!!!!

Naughty By Nature

Date: Sunday, October 18
Time: 10:00 pm – 3:00 am
Location: Blanche Restaurant & Lounge
Tickets: $20.00
Summary: Get ready to unleash your wild side with vibes that’ll keep you moving all night long.

Card Board Game Night

Date: Monday, October 19
Time: 5:00 pm
Location: The Shadowbox Theatre
Summary: Only at The Shadowbox Theatre on the 3rd Monday of every month: Card Board Game Night!

Operation Defend the North 2026 Windsor

Date: Tuesday, October 20
Time: 9:00 am
Location: St. Clair College
Summary: Operation Defend the North (ODTN) 2026 Windsor is a national cybersecurity readiness exercise hosted by St. Clair College and presented by siberX. Taking place on October 20, 2026, at the St. Clair College Centre for the Arts, the event brings together executives, cybersecurity professionals, government leaders, critical infrastructure operators, and industry stakeholders for an immersive cyber crisis simulation.

Food Handler Certification Exam - Masonic Temple, Windsor

Date: Tuesday, October 20
Time: 2:30 pm – 3:30 pm
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.

Italian Culture Lecture Series – The History of the Italian Language: From Latin to Today

Date: Tuesday, October 20
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. October 20th – The History of the Italian Language: From Latin to Today presented by Fabio Bernabo