Windsor, Thanksgiving Monday falls right in the middle of this one.
This week (Oct 8–15) Jimmy Carr brings his biggest tour yet to the WFCU Centre, Whiskey Myers rocks The Colosseum at Caesars, and Heimat Oktoberfest returns for round two downtown. Add Dear Evan Hansen at the Capitol Theatre and live comedy from Windsor Laughs, and there's plenty to do before — and after — the long weekend.
Here's your full guide to the best of Windsor-Essex this week.

🎃 October 31 – Halloween Party
6:00 PM Doors • 7:00 PM Dinner • 9:00 PM Dancing | Skyline Ballroom, Chrysler Theatre

Get ready for a frightfully fun Halloween night with a three-course plated dinner, music, and dancing. Come dressed in a costume or your favourite party attire and enjoy a spooky night out with friends. Costumes are optional, but fun is mandatory! 👻🎃💃

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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 8 – Whiskey Myers with The Ransom Brothers
7:00 PM | The Colosseum at Caesars Windsor
Whiskey Myers is scheduled to perform at The Colosseum with special guest The Ransom Brothers. The genre-blending Southern rock band, which emerged in 2007, has performed thousands of live shows during its career.

🎶 October 9 – Crissi Cochrane “Fire Sign” Vinyl Release Show
7:30 PM | Meteor
Celebrate the official release of Fire Sign, the seventh record from Canadian singer-songwriter Crissi Cochrane.

🎤 October 9 – Sing Pitch Perfect with Deke Sharon & Splush
8:00 PM | Chrysler Theatre
Join legendary a cappella expert Deke Sharon, known as the “Father of Contemporary A Cappella,” for an interactive evening inspired by the Pitch Perfect movie franchise.

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

😂 October 10 – Hannah Osborne LIVE Comedy
8:00 PM | The Tipsy Toucan
WINDSOR LAUGHS PRESENTS: Hannah Osborne has been preforming all over the Midwest since 2019.

🎤 October 12 –  Dan Duvall: Live at Windsor Laughs
8:00 PM | The Tipsy Toucan
Dan Duvall brings his ‘Pretty Good Comedy’ filled with punchy comedy and stories of his past to Windsor for one-night only!

😂 October 13 – Jimmy Carr Live at the WFCU Centre
See event details | WFCU Centre
Global comedy superstar Jimmy Carr returns to Canada with his biggest national tour yet, bringing his distinctive stand-up comedy to Windsor for a special live performance at the WFCU Centre.

😂 October 13 – Phongheads Comedy Showcase
8:30 PM – 9:30 PM | Downtown Windsor
Enjoy a weekly stand-up comedy showcase featuring a rotating lineup of local and touring comedians.

🍻 October 9-10 – Heimat Oktoberfest
See event details | 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

🎨 October 8–15 – Beyond the Pink Ribbon: The Art of Survival
See event details | ARTSPEAK Gallery
Explore Beyond the Pink Ribbon: The Art of Survival, a juried art exhibition made possible through a generous grant from the Windsor Endowment for the Arts. The exhibition brings together creative perspectives exploring survival and resilience through art.

👧 October 14 – International Day of the Girl Breakfast – Build a Dream
8:00 AM – 12:00 PM | St. Clair College Centre for the Arts
Build a Dream hosts its 9th Annual International Day of the Girl Stakeholder Breakfast, bringing together community leaders and supporters to celebrate girls, highlight opportunities, and inspire conversations around their futures and potential

Enjoy markets, shows, fashion at Windsor.

🎨 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 – Free Introductory Tai Chi Class
See event details | Fung Loy Kok Institute of Taoism
Discover the gentle practice of Taoist Tai Chi® at this free introductory class and Open House.

🍂 October 9 – Fall on the Farm: Night Market Edition
See event details | Denver’s Homestead
As the sun sets, Denver’s Homestead comes alive for a special Fall on the Farm: Night Market Edition.

🍂 October 9 – Thanksgiving Stroll the Street
See event details | Notre Dame Street
Celebrate the season of gratitude at Stroll the Street, an upbeat urban experience with small-town charm. Enjoy festive fall activities, local delights, and a welcoming community atmosphere designed for locals of all ages.

🎭 October 9–10 – Dear Evan Hansen – Arts Collective Theatre
8:00 PM | The Capitol Theatre
Arts Collective Theatre presents Dear Evan Hansen, a contemporary musical exploring connection, honesty, belonging, and the impact of a single moment

🎬 October 10 – A Charlie Brown Double Feature!
7:00 PM | Chrysler Theatre
Gather the family for a fun-filled Family Movie Night at the Chrysler Theatre! Enjoy a special double feature featuring the beloved Peanuts characters in a relaxed, family-friendly theatre setting. 

🥕 October 10 – Downtown Windsor Farmers’ Market
See event details | Downtown Windsor, Pelissier & Maiden Lane
Discover farm-fresh fruit, vegetables, produce, and unique artisan food products at the Downtown Windsor Farmers’ Market.

🛍️ October 10 – Lakeside Market
8:00 AM – 1:00 PM | 927 St. Joachim L’Association
Discover the Lakeside Market, presented by Lakeside Home Solutions, bringing together local farmers, growers, makers, artisans, small businesses, food vendors, and community organizations.

🍁 October 10 – LaSalle Autumn Market
See event details | Event Centre at LaSalle Landing
Celebrate the harvest season at the LaSalle Autumn Market, bringing together local makers, bakers, and growers for a cozy day of shopping, seasonal finds, and festive fall fun.

👻 October 8–17 – The Pet by Shane Devon Nelson
See event details | The Shadowbox Theatre
Experience a brand-new work of psychological horror this spooky season with The Pet by Shane Devon Nelson.

🛍️ October 11 – Lakewood Mini Market
See event details | Lakewood Park
Shop local and support the community at the Lakewood Mini Market! Browse local vendors, handmade goods, delicious treats, and plenty of unique finds while enjoying a vibrant community market atmosphere.

🎨 October 15 – Mystery Mural Project Paint Night
6:00 PM – 7:30 PM | The Bank Theatre
Become part of The Bank Theatre’s history with the Mystery Mural Project Paint Night! Bring your friends and family, get creative, and paint together as you help create a special mural for the theatre. 

Enjoy games, trivia and dinner nights in Windsor.

🎉 October 8- Autumn in the Vineyard
6:30 PM | Paglione Estate Winery
Join us for a cozy autumn evening of wine, food, and a little creativity. We’re hosting an intimate Charcuterie Masterclass & Wine Pairing, where you’ll learn how to build and style a beautiful charcuterie board.

🥃 October 8– Kingsville Sip & Savour Speak Easy
6:00 PM | Banded Goose Brewing Co.
Step back into the 1920s for an evening of secret sips, great bites, and good company in downtown Kingsville.

🌌 October 10 – Dark Sky Night
7:30 PM | Point Pelee National Park
Explore Point Pelee National Park after dark and experience the beauty of its dark skies. Stay late to enjoy the peaceful nighttime atmosphere

🇮🇹 October 13 – Italian Culture Lecture Series – Comedia Dell Arte
See event details | Giovanni Caboto Club
Explore Italian culture this fall with the Italian Culture Series, featuring five fascinating lectures covering Italian history, language, wine, art, and more.

📚 October 8–15 – Encore Productions Presents: Whisky, Water and Wild Times
See event details | Essex County Library – LaSalle Branch
Step back into the Roaring Twenties and explore the fascinating history of Prohibition, when the Detroit River became one of the busiest smuggling routes of the era.

🥃 October 8-15 – Trivia Night at the Manchester Bar
7:00 PM | The Manchester Bar
Weekly trivia night at The Manchester Bar in Downtown Windsor, open to all with prizes for top teams.

🎲 October 14 – Game Nights @ Central Library for Kids!
6:00 PM – 8:00 PM | Windsor Public Library – Central Branch
Enjoy a free weekly drop-in game night for kids at the Central Library in Downtown Windsor.

🎹 October 15 – Dueling Pianos Dinner, Live Music and Dancing
6:00 PM | Caboto Club of Windsor
Enjoy an evening of dueling pianos, dinner, live music, and dancing presented by the Rotary Club of Tecumseh-Lakeshore. The event supports Kiwanis Club’s Camp Sunshine, a local overnight camp helping provide children with an opportunity to enjoy a summer camp experience.

🎹 October 15 – Dueling Pianos Soiree: Live Music By Request, Dinner, and Dancing
See event details | Giovanni Caboto Club
Join the Rotary Club of Tecumseh-Lakeshore and the Kiwanis Club for an evening of live music, dinner, dancing, and fun at the Caboto Club.

Enjoy the sports events in Windsor of your choice!

🏒 October 9 – Windsor Lancers Hockey
7:30 PM | Adie Knox Herman Arena
Catch the Windsor Lancers in action as they take on Lakehead on Friday, October 9. Experience an exciting night of university hockey as the Lancers hit the ice at Adie Knox Herman Arena.

⚽ October 9 – Windsor Lancers Soccer
6:00 PM (W) & 8:00 PM (M) | Alumni Stadium
Catch the Windsor Lancers in action as they take on Algoma in an exciting evening of university soccer.

🎳 October 10 – 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.

🐾 October 12 – Saginaw Spirit vs. Windsor Spitfires – Paws and Pucks
See event details | WFCU Centre
Hockey is better with your best friend by your side! Paws and Pucks brings a unique game-day experience featuring pet-friendly activities and plenty of fun for pets and their humans.

That's your week across Windsor-Essex. Whether you're rocking out with Whiskey Myers at Caesars, catching A Charlie Brown Double Feature with the family, or getting into the spirit at the Thanksgiving Stroll the Street, there's plenty to enjoy before the long weekend hits. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse