Windsor, Halloween week has officially arrived.
This week (Oct 29–Nov 5) WIFF 2026 kicks off ten days of film across the city, Evil Dead: The Musical brings horror-comedy mayhem to KordaZone Theatre, and Scarehouse Windsor wraps up its final haunted nights. Add the Ghost Walk of Historic Sandwich Town, trick-or-treat events across Essex and Kingsville, and live comedy from Windsor Laughs, and there's no shortage of ways to spend your week. Here's your full guide to the best of Windsor-Essex this week.

🎄 November 1 – My Letter to Santa Holiday Market
10:00 AM – 3:00 PM | LaSalle Event Centre, 970 Front Road, LaSalle

✨ THE COUNTDOWN TO THE HOLIDAYS IS ON! ✨

Get into the holiday spirit at the annual My Letter to Santa Holiday Market! 🎁 Discover 100+ local vendors offering handmade gifts, unique crafts, festive decorations, and delicious treats while supporting small businesses. Enjoy a coffee bar, food trucks, a Santa letter-writing station, and digital photos with Santa. Santa will also be handing out special treats to children from 12 PM – 2 PM, while supplies last. Best of all, admission and parking are free! 🎅✨🎄

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🏍️ 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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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 29 – November 8 – Windsor International Film Festival (WIFF) 2026
Capitol Theatre & venues across Windsor
Canada's largest volunteer-run film festival kicks off this week with daily screenings of Canadian and international films across multiple venues. The WIFF Box Office is located at 109 University Ave W (cashless). Don't miss the special WIFF Dinner and Movie event at Chrysler Theatre on November 2 and the SNIFF Night 2 volunteer appreciation showcase on November 5.

🎭 October 30 – Bill Nuvo: Out of the Box – A Tribute to Houdini
7:00pm | The Shadow Box Theatre
A special Halloween-week tribute performance celebrating the legendary Houdini at Windsor's intimate Shadow Box Theatre. A one-night theatrical experience blending magic, storytelling, and live performance.

🎶 October 30 – Fall Concert Series – First Lutheran Church
First Lutheran Church
The ongoing fall concert series continues with a live performance at First Lutheran Church, showcasing local and guest musicians in a welcoming community setting.

🎸 November 1 – Pickle Me Softly
Wolfhead Distillery
Live music at Wolfhead Distillery in Amherstburg — enjoy craft spirits, food, and a relaxed atmosphere with Pickle Me Softly performing on the weekend.

🎤 November 3 – Open Mic at The Grovedale
7:00pm | The Grovedale, Kingsville
Open mic night in Kingsville — bring your talent or just come to listen and enjoy an evening of local performers at The Grovedale.

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

😂 October 30 – Leo Dufour LIVE Comedy at Tipsy Toucan
The Tipsy Toucan, 1444 Ottawa St
Windsor Laughs presents Leo Dufour for a night of professional stand-up comedy at Windsor's only comedy club.

🎙️ November 3 – Phongheads Comedy Showcase
8:30pm – 9:30pm | Phog Lounge, 157 University Ave W
Free weekly stand-up comedy showcase mixing new comics and seasoned performers at downtown Windsor's iconic Phog Lounge. Doors 8pm, cash bar.

🏛️ October 29–30 – Fighting in Flanders Exhibition
8:30am | LaSalle
A special exhibition honouring Canadian service in Flanders during the World Wars, on display at LaSalle — visit ahead of Remembrance Day.

👶 October 30 – Essex BIA – Halloween Tiny Tot Parade
10:00am | Downtown Essex
The Essex BIA's adorable Halloween parade for the littlest trick-or-treaters — dress up the kids and join the fun through downtown Essex.

🎃 October 30 – Halloween Spooktacular
4:30pm | Essex
A community Halloween celebration with activities, treats, and spooky fun for all ages in the Town of Essex.

🤠 October 30 – Harvest Hoedown
Cooper's Hawk Vineyards, Harrow
Celebrate harvest season with a hoedown at scenic Cooper's Hawk Vineyards — enjoy a 90-minute beginner line dance lesson, open dancing, amazing food, and incredible wine all in one festive evening.

🎃 Through October 31 – Scarehouse Windsor Haunted Experiences
Scarehouse Windsor, 1441 McDougall St, Windsor
Scarehouse Windsor is back and more haunting than ever with over 5 unique chilling walk-through experiences. Last chance this season — the final nights run October 28–31. VIP immersive dining with Nico Taverna available October 29-30

🏚️ October 31 – Ghost Walk of Historic Sandwich Town
11:00am | Local History Branch, Windsor Public Library
Explore the haunted history of one of Ontario's oldest settlements on this guided Halloween walk through historic Sandwich Town. Hear real ghost stories and discover the eerie past of Windsor's founding neighbourhood — the perfect Halloween morning activity.

🗺️ Through October 31 – CROSSROADS Haunted History Pass
Self-guided | Windsor-Essex region
A free self-guided pass to discover the region's most mysterious stories and spookiest historic places. Register online for your digital pass and explore at your own pace.

🍺 October 31 – Halloween Costume Party at Walkerville BOOwery
7:00pm | Walkerville Brewery
Walkerville Brewery transforms into BOOwery for Halloween night — costumes encouraged, craft beer flowing, and a spooky atmosphere in one of Windsor's favourite breweries.

🚗 October 31 – Trunk or Treat
6:00pm | Essex
Families decorate their car trunks and hand out candy — a safe, fun trick-or-treat alternative for kids of all ages in Essex.

🍬 October 31 – Trick or Treat Kingsville
11:00am | Kingsville
Trick-or-treating event in downtown Kingsville — businesses along the main street welcome costumed kids and families for a safe daytime Halloween experience.

📸 October 31 – Nostalgic Photo Booth: Hallowe'en Edition
4:00pm | Windsor Public Library – Central Branch
Get your Halloween costume photo taken at the library's retro-style photo booth — free, fun, and perfect for keeping a memento of your spooky outfit.

🎃 November 1 – Pumpkin Parade
6:00pm | Essex (also in Kingsville at 12:00pm & 6:00pm)
Bring your carved jack-o'-lanterns to light up the night in this community pumpkin display — events happening in both Essex and Kingsville on November 1.

🎨 November 1 – Watercolours and Wine at Cooper's Hawk Vineyards
Cooper's Hawk Vineyards, Harrow
Join Art Windsor-Essex for a free guided watercolour painting workshop at Cooper's Hawk Vineyards — all materials provided, all skill levels welcome. Pre-registration required; spots are limited.

🚋 Weekends – Streetcar No. 351 Fall Hours
11:00am – 5:00pm | Michael D. Hurst Legacy Park
The heritage streetcar has shifted to fall weekend-only hours — ride the restored 1920s streetcar through the park on Saturdays and Sundays.

💜 November 3 – Woman Abuse Prevention Month – Tree Lighting
6:00pm | Essex
A community tree-lighting ceremony in Essex marking Woman Abuse Prevention Month — raising awareness and showing solidarity through a meaningful public gathering.

Enjoy markets, shows, fashion at Windsor.

🎷 October 29 – November 5 – Chimczuk Museum: 50 Years of Jazz Concert Promotion in Windsor
Chimczuk Museum
A special exhibit celebrating 50 years of jazz concert promotion in Windsor — exploring the people, venues, and performances that built the city's jazz scene.

🍷 October 29 – Winemaker and Brewmaster Dinner
6:00pm – 9:00pm | Erie St GastroPub, 839 Erie Street East
An evening of Ontario wine and craft beer paired with four delicious courses curated by Chef Iris Lynh Le — choose your wine or beer pairing and enjoy a guided tasting experience. Tickets $110.

🎭 October 29–31 – Evil Dead: The Musical at KordaZone Theatre
KordaZone Theatre, 2520 Seminole St, Windsor
The cult classic horror-comedy musical returns to KordaZone Theatre — five college students, an abandoned cabin, demons, chainsaws, and a Splatter Zone where audience members get covered in fake blood. Pure comedy start to finish.

🎭 October 30 – November 1 – The Bank Theatre Presents: Farce of Habit!
The Bank Theatre, 10 Erie St S, Leamington | Oct 30 @ 7:30pm, Oct 31 & Nov 1 @ 2:00pm
A hilarious Jones, Hope, Wooten comedy directed by Mark Ribble at Leamington's Bank Theatre — the Wilburn family is back at the fishing lodge dealing with habits in more ways than one. Tickets $25+HST.

🎭 October 30 – Friedreich's Fighters Fundraiser – Fright Night
7:00pm – 1:00am (Doors 6:30pm) | Chrysler Theatre
A Fright Night fundraiser supporting Friedreich's ataxia research with a spooky evening at the Chrysler Theatre. Adults $75, students $40.

🎃 October 31 – Halloween Party
Doors 6:00pm, Dinner 7:00pm, Dancing 9:00pm | St. Clair Centre for the Arts, Skyline Ballroom
St. Clair College Centre for the Arts' annual Halloween Party featuring dinner, dancing, and costumes in the Skyline Ballroom. Tickets $59.95+tax.

🛒 October 31 – Lakeside Market
927 St Joachim L'Association, 2722 County Rd 42, Lakeshore
A vibrant market celebrating the bounty of Essex County — local farmers, artisans, food vendors, and family-friendly experiences all under one roof at this seasonal community market.

🥕 October 31 – Downtown Windsor Farmers' Market
9:00am – 2:00pm | Pelissier Street (between Wyandotte & Park)
Farm-fresh fruit, vegetables, artisan food products, a Kids Corner, art exhibits, entertainment, and food demonstrations at downtown Windsor's beloved weekly farmers' market.

🎄 November 1 – My Letter to Santa Annual Holiday Market
10:00am | LaSalle
An annual holiday market in LaSalle featuring local vendors, gifts, and festive shopping — get a head start on your holiday list while supporting local makers.

🎬 November 2 – As Far Back As I Can Remember – WIFF Dinner and Movie
Doors 5:00pm, Dinner 5:30pm, Movie 7:30pm | Chrysler Theatre
A special Windsor International Film Festival dinner-and-movie evening presented by WIFF and St. Clair College Centre for the Arts at the Chrysler Theatre.

Enjoy games, trivia and dinner nights in Windsor.

🧠 October 29 – Trivia Night at The Manchester Bar
7:00pm – 9:00pm | The Manchester Bar, downtown Windsor
Weekly trivia night hosted by BRN Trivia every Thursday at The Manchester Bar. Free entry with prizes for winners — grab your team and test your knowledge.

🔒 November 3 – Cybersafe Seniors: Preventing AI Fraud and Scams
St. Mark's by-the-Lake Anglican Church
A free community workshop helping seniors recognize and avoid AI-powered fraud and online scams — practical tips to stay safe in the digital age.

🏛️ November 3 – Italian Culture Lecture Series – Italy's Most Influential Architectural Masterpieces
Giovanni Caboto Club, 2175 Parent Ave, Windsor
Explore the architectural masterpieces that shaped Italy's identity in this free public lecture presented by Frank Perissonotti — come early for dinner at the Caboto Club Bar & Pizzeria.

🥃 November 4 – Whisky Wednesdays – The Pairing Experience: The Apple & The Barrel
Windsor
A curated whisky pairing experience exploring the flavours where apple meets barrel — a guided tasting evening for whisky enthusiasts and curious newcomers alike.

🍝 November 4 – Caboto Club Charity Pasta Night
Giovanni Caboto Club
A charity pasta night at Windsor's Giovanni Caboto Club — enjoy a hearty Italian dinner while supporting a good cause in the community.

♻️ November 4 – E-Waste Collection Drive
10:00am | LaSalle
Drop off your old electronics for safe recycling at LaSalle's e-waste collection drive — free community event to keep electronics out of the landfill.

📚 November 5 – Leamington Comic Jam
Leamington
A comic book and illustration jam session in Leamington — bring your pens, sketchbooks, and creativity for an evening of collaborative drawing and storytelling.

🧠 November 5 – Trivia Night at The Manchester Bar
7:00pm – 9:00pm | The Manchester Bar, downtown Windsor
Weekly trivia night hosted by BRN Trivia every Thursday at The Manchester Bar. Free entry with prizes for winners — grab your team and test your knowledge.

🎬 November 5 – Sniff Night 2 – The WIFF Volunteer Appreciation Showcase
Windsor
A special WIFF screening event honouring the volunteers who make the festival possible — enjoy film, food, and community at this appreciation night.

Enjoy the sports events in Windsor of your choice!

🏒 October 29 – Windsor Spitfires vs Erie Otters
7:05pm | WFCU Centre, Windsor
OHL regular-season home game as the Windsor Spitfires host the Erie Otters at the WFCU Centre. Grab your tickets and cheer on the Spits!

🏀 October 30 – Windsor Lancers Basketball
6:00pm | Toldo Lancer Centre
University of Windsor Lancers take the court at the Toldo Lancer Centre — catch OUA basketball action and support the home team.

🎳 October 31 – Forest Glade Optimist Junior Bowling
SuperBowl Lanes
Youth bowling league organized by the Forest Glade Optimist Club — a fun Saturday activity for kids and families at SuperBowl Lanes.

That's your week across Windsor-Essex. Whether you're catching a WIFF 2026 screening, haunting it up at Scarehouse Windsor, or getting a head start at the My Letter to Santa Holiday Market, there's plenty to keep you busy before Halloween wraps up. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse