Windsor, Halloween week is here.
This week (Oct 22–29) Evil Dead: The Musical brings horror-comedy mayhem to Kordazone Theatre, Dreamer: Supertramp Experience hits the Chrysler Theatre stage, and the WSO goes country with Genevieve Fisher at the Capitol. Add truck-or-treat events in LaSalle and Tecumseh, a Halloween-themed Spitfires game, and comedy from Windsor Laughs, and there's plenty to do before the 31st arrives.
Here's your full guide to the best of Windsor-Essex this week.

🏍️ November 14 – FMX World Tour: Stars of Freestyle Motocross
Pit Party 1:00 PM – 2:00 PM | Show 2:30 PM | WFCU Centre, 8787 McHugh Street, Windsor

Get ready for an explosive, full-throttle afternoon as the world’s top freestyle motocross riders defy gravity! 🔥 Watch elite athletes soar through the air with jaw-dropping tricks like Superman Seat Grabs, Cliff Hangers, Kiss of Death, Back Flips, Super Backflips and more. With roaring engines, mid-air rotations and heart-stopping landings, this high-octane show is packed with adrenaline for seasoned fans and first-timers alike.

Arrive early for the Pit Party to get up close with the riders and their machines before the action takes off! 🏁💨🤘

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🎃 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 24 – Dreamer: Supertramp Experience
8:00 PM | Chrysler Theatre
Relive the timeless sound of Supertramp with Dreamer: Supertramp Experience, a live tribute celebrating the legendary band's iconic music. Enjoy an evening filled with classic hits and memorable melodies.

🎻🤠 October 24–25 – WSO Goes Country with Genevieve Fisher
7:30 PM | Capitol Theatre
Get ready for a country music experience like no other as the Windsor Symphony Orchestra teams up with country singer Genevieve Fisher!

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

😂 October 23 – Jeff Leeson: Only Gonna Say This Once Comedy Tour
8:00 PM | Chrysler Theatre
Get ready for a night of laughter as internationally touring comedian Jeff Leeson brings his Only Gonna Say This Once Comedy Tour to Windsor!

🎤 October 24 – Ben Bayfield LIVE Comedy at Tipsy Toucan
8:00 PM | The Tipsy Toucan
Windsor Laughs presents Toronto-based comedian and rostered Yuk Yuk's performer Ben Bayfield for a night of observational, witty stand-up.

🕵️🎃 October 24 – Murder at Water’s Edge: Halloween Edition
8:00 PM | Water’s Edge Event Centre
Put your detective skills to the test at Murder at Water’s Edge: Halloween Edition, an interactive stand-up comedy murder mystery!

🎭 October 27 –  Phongheads Comedy Showcase
8:30 PM | Phog Lounge,
Free weekly stand-up showcase mixing new comics and seasoned performers; doors 8pm, cash bar.

🧙‍♀️ October 22–23 – Scream Queens: Songs of Spells and Shadows
See event details | Willistead Manor
Step into a world of haunting melodies and mysterious magic with Scream Queens: Songs of Spells and Shadows, presented by Abridged Opera! Set inside the historic Willistead Manor, this unique musical experience blends opera, theatrical storytelling, and spooky seasonal atmosphere for an unforgettable Halloween gathering.

🚒October 24 - Lasalle Truck Or Treat
12:00–4:00pm · Vollmer Complex, 2121 Laurier Parkway, LaSalle
Trick-or-treat among a lineup of emergency, construction, and specialty vehicles at this Town of LaSalle family Halloween event.

October 24 - OPTIMIST St. Clair Beach Trunk or Treat
5:30pm · Lacasse Park, Tecumseh
A neighbourhood trunk-or-treat hosted by the Optimist Club of St. Clair Beach, with decorated car trunks handing out candy to costumed kids.

🎃 October 24 – North Star High School PUMPKINFEST ’26
See event details | North Star High School
Get ready for a fun-filled day of shopping and community spirit at PUMPKINFEST ’26! North Star High School’s annual vendor market fundraiser returns with an impressive lineup of 200+ vendors, offering plenty of opportunities to discover unique products.

🍬 October 24 – 21st Annual Trick or Treat @ St. Clair Shores Shopping Centre
11:00 AM | Lakeshore
Get ready for a spooktacular Halloween outing at St. Clair Shores Shopping Centre! Trick-or-treat at over 35 participating shops, enjoy face painting, snap fun pictures at the photo booth, and meet balloon twisters. Bring the family, dress up in your favourite Halloween costumes, and enjoy a morning full of festive fun!

Enjoy markets, shows, fashion at Windsor.

🧟 October 22–24 & October 29–31 – Evil Dead: The Musical
See event details | Kordazone Theatre
Get ready for a thrilling night of horror, comedy, and musical theatre with Evil Dead: The Musical! This stage adaptation brings together elements of The Evil Dead, Evil Dead 2, and Army of Darkness, turning the cult horror stories into a wildly entertaining theatrical experience.

🛍️ October 23 – RCL Br# 644 Vintage Night Market
4:00 PM | Royal Canadian Legion Branch #644
Discover unique treasures and vintage finds at the RCL Br# 644 Vintage Night Market! Featuring more than 20 vendor tables, this market is the perfect place to browse curated vintage pieces, uncover one-of-a-kind items, and find something special.

🍂🎨 October 24 – Fall Artisan Open House
5:00 PM | Sun Parlour Curling Club
Celebrate the season at the Fall Artisan Open House in Leamington! Browse local artisan vendors, discover handmade creations, and enjoy tasty BBQ along with coffee and tea.

🎃🍁 October 24 – Pumpkins, Treats & Treasures Market
10:00 AM | St. Paul’s Anglican Church
Celebrate autumn at the Pumpkins, Treats & Treasures Market in Essex! Browse local vendors, discover unique finds, and treat yourself to delicious baked goods while enjoying the cozy fall atmosphere.

🧺 October 24 – RCL Br# 644 Indoor/Outdoor Yard Sale & Vendor Market
9:00 AM | Royal Canadian Legion Branch #644
Hunt for great finds at the RCL Br# 644 Indoor/Outdoor Yard Sale & Vendor Market! With more than 20 tables featuring yard sale items and vendor goods, you can browse a variety of unique treasures, useful finds, and unexpected bargains.

🕯️ October 24 – Void Market: Dark Harvest Market
12:00 PM | St. Cyril’s Slovak Centre
Step into the unusual at Void Market: Dark Harvest Market, presented by Into the Void Market! Explore a curated collection of makers, artists, and vendors showcasing eerie creations, unusual finds, and macabre-inspired art.

🍎 October 24 – Lakeside Market
8:00 AM – 1:00 PM | Windsor-Essex
Start your Saturday with a visit to the Lakeside Market, presented by Lakeside Home Solutions! Explore a lively gathering of local farmers, growers, makers, and artisans offering fresh produce, handmade creations, and unique finds.

🥕 October 24 – Downtown Windsor Farmers’ Market
See event details | Downtown Windsor
Discover fresh local flavours at the Downtown Windsor Farmers’ Market! Browse a variety of farm-fresh fruits and vegetables, explore unique artisan food products, and support regional farmers and local producers.

🎬October 24- Movie Trivia with Mack Flash at Walkerville Brewery
7:00–9:00pm I Walkerville Brewery
Lights. Camera. TRIVIA! Join us at Walkerville Brewery for a night of movie magic with the one and only Mack Flash!

🎁 October 25 – Lakeshore Helping Lakeshore’s 2nd Annual Craft & Gift Show
See event details | Lakeshore, Ontario
Discover unique handmade creations and thoughtful gifts at Lakeshore Helping Lakeshore’s 2nd Annual Craft & Gift Show!

🛍️ October 25 – Lakewood Mini Market
See event details | Lakewood Plaza
Spend your Sunday discovering local finds at the Lakewood Mini Market! This recurring community market brings together local vendors offering unique products and special discoveries in a welcoming plaza setting.

🃏 October 25 – Rad Sports Card and TCG Show
10:00 AM – 4:00 PM | St. Clair College SportsPlex
Calling all collectors and trading card fans! The Rad Sports Card and TCG Show brings together more than 100 vendor tables featuring sports cards and trading card games.

🍂 October 25 – Fall Leaf Garland: Printmaking Art Workshop
See event details | Windsor
Celebrate the beauty of autumn with a creative, family-friendly art workshop! Explore printmaking techniques to create your own fall leaf garland, inspired by the colours and textures of the season.

📜 October 25 – Rum Runners Tour — SOLD OUT
See event details | Windsor, Ontario
Step back into Windsor’s fascinating Prohibition-era history with the Rum Runners Tour by Encore Productions! Discover stories from the days when secret smuggling routes and underground networks connected Windsor to the United States across the Detroit River.

Enjoy games, trivia and dinner nights in Windsor.

🥂 October 22 – The Perfect Pouring Dinner Series: The Art of Autumn
The Perfect Pouring Dinner Series
After a little summer hiatus, our Perfect Pouring Dinner Series returns with The Art of Autumn, an evening of great food, great beer, and the kind of pairings that make you stop mid-bite and go back for another sip.

🎃 October 22 – Painting Night “Halloween Pumpkin”
7:00 PM | Eastwood's Grill & Lounge
A guided Halloween-themed paint night; no experience needed, just good vibes and a fun night out with friends.

🧠 October 22 – Trivia night at The Manchester Bar
7:00 PM | The Manchester Bar
Weekly free trivia with BRN Trivia, drink specials and prizes for winning teams.

🏳️‍🌈 October 22 – Pride Dirty Bingo
8:00 PM | VILLAIN'S BEASTRO
Join us Thursday, October 22, 2026 at 8:00pm at VILLAIN’s BEASTRO for an adults-only evening where classic bingo gets a playful Pride Fest twist, complete with our gracious hosts Venom Von Snap and B Martini giving you campy commentary, music, and plenty of surprises.

👻 October 23 – Family Monster Mash
6:00–8:00 PM | Lakeside Park Pavilion, Kingsville
Get ready for a spooktacular evening of Halloween fun at Family Monster Mash! Enjoy music, dancing, interactive games, and exciting Halloween activities for the whole family.

🍇 October 23 – Wines for the world
6:00 PM | St. Clair Centre for the Arts
Experience wines from our local wineries and sample culinary delights from our region’s restaurants. Craft beer will also be featured this year. Enjoy the music of Oxley Duo.

🕵️ October 24 – Gatsby Murder Mystery Dinner Cruise
See event details | Detroit River
Step into the glamour and intrigue of the Roaring Twenties with the Gatsby Murder Mystery Dinner Cruise! Set against the scenic backdrop of the Detroit River, this themed evening combines a mysterious storyline with the elegance of the Gatsby era.

🎬 October 24 – NFB Animation Night
7:00 PM · Villa92 Eatery and Cultural House, Tecumseh
Celebrate World Animation Day with a special screening of classic National Film Board animated shorts! Revisit beloved Canadian animation favourites, including The Sweater and The Big Snit, and enjoy an evening celebrating creativity, storytelling, and the art of animation.

🏚️ October 25 – Haunted House Art Workshop: Family and Friends Halloween Craft
2:30 PM | Expressive Brush Art Studio
Get creative this Halloween with a fun, hands-on art workshop for all ages! Build and decorate your very own spooky haunted house while enjoying a festive crafting experience with family and friends.

🇮🇹 October 27 – Italian Culture Lecture Series – Learning About Wines
7:00 PM | Giovanni Caboto Club
The Giovanni Caboto Club is proud to present our Fall Italian Culture Lecture Series, featuring five engaging evenings exploring the rich history, traditions, language, arts, architecture, and culture of Italy.

🎯 October 29 – Trivia night at The Manchester Bar
7:00 PM | The Manchester Bar
Weekly free trivia with BRN Trivia, drink specials and prizes for winning teams.

🍷 October 29 – Winemaker and Brewmaster Dinner
6:00 PM | Erie St Gastro Pub
Join hosts Allison Christ and Eric Robert for an exciting night of Ontario wine and craft beer paired with four delicious courses specially curated by Chef Iris Lynh Le.

Enjoy the sports events in Windsor of your choice!

🏒 October 23–24 – Windsor Lancers Hockey
October 23 at 7:30 PM & October 24 at 4:00 PM | Adie Knox Herman Arena
Get ready for an exciting weekend of hockey as the Windsor Lancers take on Ottawa in back-to-back matchups!

🎳 October 24 – Forest Glade Optimist Junior Bowling
See event details | SuperBowl Lanes, Windsor
Looking for a fun activity for kids? The Forest Glade Optimist Junior Bowling League gives children the chance to learn bowling, develop their skills, and make new friends along the way.

🏒🎃 October 24 – Soo Greyhounds vs. Windsor Spitfires – Halloween Game
See event details | WFCU Centre
Get ready for a spooky night of hockey as the Windsor Spitfires take on the Soo Greyhounds in a special Halloween-themed game!

🏃 October 24 – WYCked Run 5K
9:00–9:30 AM | Windsor Riverfront, Dieppe Gardens
Put on your favourite costume and get moving at the WYCked Run 5K! This fun, costumed community run/walk brings people of all ages together for a morning of fitness, Halloween spirit, and community connection along Windsor’s beautiful waterfront.

🎳 October 25 – BOWL-A-WEEN
3:00 PM | Rev's Rose Bowl, Dougall Avenue
Get into the Halloween spirit with BOWL-A-WEEN, a spooky-themed bowling party at Rev's Rose Bowl! Gather your friends and family for an afternoon of bowling fun and festive Halloween vibes.

🏇 October 25 – Leamington Raceway Horse Races
1:00 PM | Leamington Raceway
Enjoy an afternoon of live horse racing at Leamington Raceway! Experience the excitement of race day as horses and jockeys take to the track for an engaging sporting event.

🏒 October 28 – 2026 IIHF Women's World Championship Pre-Tournament
See event details | WFCU Centre, Windsor
Get ready for an exciting night of international hockey as Canada's National Women's Hockey Team takes on its biggest rival ahead of the 2026 IIHF Women's World Championship!

🏒 October 29 – Erie Otters vs. Windsor Spitfires – Remembrance Day
See event details | WFCU Centre, Windsor
Catch an exciting OHL matchup as the Windsor Spitfires take on the Erie Otters in a special game honouring veterans and service members.

That's your week across Windsor-Essex. Whether you're catching Evil Dead: The Musical at Kordazone, trick-or-treating with the kids in LaSalle or Tecumseh, or cheering on the Spitfires in their Halloween game, there's plenty to fill your calendar before the 31st arrives. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse