Windsor, the fall lineup keeps building.
This week (Oct 15–22) the Kingsville Migration Festival celebrates bird conservation, Dear Evan Hansen lands at the Capitol Theatre, and Evil Dead: The Musical brings horror-comedy mayhem to Kordazone Theatre. Add Fleetwood Mac Mania, the Diablerie Vampire Ball, and comedy from Windsor Laughs, and there's no shortage of ways to spend your evenings.
Here's your full guide to the best of Windsor-Essex this week.

🎃 October 18 – Trick or Treat Treasures Vendor Market
10:00 AM – 3:00 PM | LaSalle Event Centre, 970 Front Road, LaSalle

Join us for a hauntingly good time featuring incredible local small businesses, delicious eats and Halloween Vibes for the whole family. Free treats for the kids (while quantities last)

Vendor Costume Contest -Cast your vote for your favourite Vendor Costume

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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 15 – Dueling Pianos with Rose City Dueling Pianos
7:00 PM | Walkerville Brewery
Get ready for an entertaining evening of live music with Rose City Dueling Pianos, featuring performers Marc Dorian and Jeremy Coulter! Enjoy a lively musical performance filled with piano talent, familiar tunes, and plenty of audience-friendly entertainment.

🎶 October 15 – Dueling Pianos Dinner, Live Music and Dancing
6:00 PM | Caboto Club of Windsor
Enjoy an evening of music, dinner, and dancing at the Dueling Pianos Soirée, presented by the Rotary Club of Tecumseh-Lakeshore in support of Kiwanis’ Camp Sunshine.

🎤 October 15 – Dueling Pianos Soirée: 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 music, dinner, dancing, and community spirit at the Dueling Pianos Soirée!

🎭 October 15–16 – Menopause The Musical
October 15 at 7:30 PM & October 16 at 8:00 PM
Get ready for an entertaining night with Menopause The Musical, presented by Shaggypup Productions!

🎸 October 17 – Fleetwood Mac Mania
8:00 PM | Chrysler Theatre, St. Clair College Centre for the Arts
Get ready for a night of classic rock with Fleetwood Mac Mania, presented by Beach Towel Communication!

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

🎤 October 16 –  Friday Comedy Session live stand up
8:00 PM | Windsor Laughs Comedy Club at The Tipsy Toucan
Weekly Friday stand-up comedy session at Windsor Laughs Comedy Club, featuring a rotating lineup of touring and local comedians.

✨ October 16 – WINDSOR SINGLES, Stand up comedy and matchmaking
7:00 PM | Meteor
Mingle. Maybe Match.” Looking to laugh and maybe meet someone new? WINDSOR Singles is a one-of-a-kind night that blends stand-up comedy with real-life matchmaking.

😂 October 17 – Standup Comedy at Sidelines Sports Bar & Grill!
8:00 PM | Sidelines Sports Bar n Grill
Come join us for THE LONGEST RUNNING MONTHLY COMEDY SHOW IN WINDSOR!!!! Standup Comedy at Sidelines Sports Bar & Grill!

🎤 October 17 –  Ben Albert: Live Stand Up Comedy
8:00 PM | Windsor Laughs Comedy Club at The Tipsy Toucan
Stand-up comedian Ben Albert headlines two shows at Windsor Laughs Comedy Club!

😂 October 20 – Phogheads Comedy Showcase
8:30 PM – 9:30 PM | Downtown Windsor
Enjoy an evening of stand-up comedy at the Phogheads Comedy Showcase, featuring a rotating lineup of local and touring comedians.

🦅 October 16–18 – Kingsville Migration Festival
See event details | Town of Kingsville
Celebrate migration, heritage, and nature conservation at the Kingsville Migration Festival! This annual community celebration honours the legacy of Jack Miner, a pioneer in bird conservation, while highlighting the importance of protecting wildlife and preserving natural habitats.

🎷 October 17 – Jazz and Blues Festival
12:00 PM | Royal Canadian Legion Branch #644
Enjoy an afternoon of smooth jazz and cool blues at the Jazz and Blues Festival in Windsor. This community event also highlights the valuable programs provided by the Royal Canadian Legion in support of Canadian veterans.

Enjoy markets, shows, fashion at Windsor.

🎨 October 15 – Mystery Mural Project Paint Night
6:00 PM – 7:30 PM | The Bank Theatre
Get creative and become part of The Bank Theatre’s history at the Mystery Mural Project Paint Night! Gather your friends and family for a fun, hands-on painting experience where you can create your own artwork while contributing to a special community project

🎭 October 15–17 – The Pet by Shane Devon Nelson
See event details | The Shadowbox Theatre
Step into a chilling world of suspense with The Pet, a brand-new psychological horror production by Shane Devon Nelson.

📚 October 15 – Whisky, Water and Wild Times
See event details | Essex County Library – Essex Branch
Travel back to the Roaring Twenties with Encore Productions’ Whisky, Water and Wild Times, an engaging look at the fascinating history of Prohibition and its impact on the Detroit River region.

🎭 October 16–18 – Dear Evan Hansen
8:00 PM | The Capitol Theatre
Experience the powerful, emotional story of Dear Evan Hansen, presented by Arts Collective Theatre. This contemporary musical explores the human need for connection, the importance of honesty, and the challenges of navigating identity and belonging.

🎭 October 16–24 – Evil Dead: The Musical
See event details | Kordazone Theatre
Get ready for a wild mix of horror, comedy, and musical mayhem with Evil Dead: The Musical at Kordazone Theatre!

🎨 October 17–18 – Art at the oTENTiks
See event details | Point Pelee National Park
Discover local creativity at Art at the oTENTiks, a unique outdoor art experience at Point Pelee National Park! Take a stroll through the Camp Henry oTENTik village, meet talented local artisans, and watch them showcase their work in a beautiful natural setting.

🥕 October 17 – Downtown Windsor Farmers’ Market
See event details | Pelissier Street
Spend a Saturday exploring the Downtown Windsor Farmers’ Market, where local flavours and community spirit come together! Browse a variety of farm-fresh fruits and vegetables, discover specialty food products, and shop unique artisan goods from talented local vendors.

🍂 October 17 – Family Fun Fall Market
10:00 AM | The Event Centre at LaSalle Landing
Enjoy a fun-filled day for the whole family at the Family Fun Fall Market in LaSalle! Browse local vendors, discover unique products, and enjoy a variety of activities designed especially for kids.

🛍️ October 17 – Lakeside Market
8:00 AM – 1:00 PM | 927 St. Joachim L’Association
Spend your Saturday morning exploring the Lakeside Market, presented by Lakeside Home Solutions! Discover a vibrant community market featuring local farmers, fresh produce, handmade goods, artisan creations, specialty foods, and unique finds from small businesses.

🛍️ October 18 – Ford City Flea Market
See event details | 1000 Block of Drouillard Road
Spend your Sunday exploring the Ford City Flea Market, a lively community event celebrating local creativity, small businesses, and neighbourhood charm!

🧺 October 18 – Tecumseh Farmers Market 2026
9:00 AM | Lacasse Park
Discover local gems at the Tecumseh Farmers Market, featured in the Hometown Highlights – Experience Local initiative!

🎸 October 18 – Beats and Booths Fall Vendor Market and Elvis Tribute
11:00 AM | LaSalle Landing Event Centre
Spend a lively Sunday at Beats and Booths Fall Vendor Market and Elvis Tribute in LaSalle! Explore a variety of vendor booths, discover unique products from local businesses, and enjoy a fun-filled atmosphere celebrating shopping, music, and community.

🎃 October 18 – Trick or Treasures Vendor Market
10:00 AM | LaSalle Landing Event Centre
Get ready for a spooktacular day of Halloween fun and local shopping at the Trick or Treasures Vendor Market! Browse a variety of unique finds from local vendors, enjoy delicious food, and soak up the festive fall atmosphere.

Enjoy games, trivia and dinner nights in Windsor.

🥃 October 15-22 – Trivia Night at the Manchester Bar
7:00 PM | The Manchester Bar
Weekly pub trivia night hosted at The Manchester Bar in Downtown Windsor, with another session also landing October 22.

📚 October 15 – ACOTAR Trivia & Costume Party
7:00 PM | Black Sage Bakery & Café
Calling all ACOTAR and Maasverse fans! Celebrate the world of Prythian at this themed trivia and costume event inspired by Sarah J. Maas’s beloved fantasy universe. Test your knowledge of the courts, characters, and storylines, show off your favourite character-inspired outfit, and connect with fellow fans ahead of the next ACOTAR release.

🦇 October 17–18 – Diablerie Vampire Ball
8:00 PM | Water’s Edge Event Centre
Step into a world of mystery, elegance, and gothic spectacle at the Diablerie Vampire Ball. Set inside a transformed decommissioned church, this immersive event promises an atmospheric evening where music, dramatic surroundings, and vampire-inspired style come together for a memorable experience.

🎲 October 19 – Card Board Game Night
5:00 PM | The Shadowbox Theatre
Calling all board game and card game enthusiasts! Card Board Game Night returns to The Shadowbox Theatre on the third Monday of the month.

🇮🇹 October 20 – Italian Culture Lecture Series: The History of the Italian Language — From Latin to Today
See event details | Giovanni Caboto Club
Discover the fascinating evolution of the Italian language at this engaging lecture in the Italian Culture Lecture Series. Explore how Italian developed from Latin into the language spoken today, uncovering the history, traditions, and cultural influences that shaped it along the way.

🧙 October 21–22 – Scream Queens: Songs of Spells and Shadows
See event details | Willistead Manor
Step into a world of haunting melodies, mysterious shadows, and Halloween magic with Scream Queens: Songs of Spells and Shadows! Presented by Abridged Opera, this unique musical experience transforms historic Willistead Manor into an atmospheric haunted house filled with spellbinding performances and eerie surprises.

🍂 October 22 – The Perfect Pouring Dinner Series: The Art of Autumn
Banded Goose Brewing Co.
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.

Enjoy the sports events in Windsor of your choice!

🏕️ October 15 – Sudbury Wolves vs. Windsor Spitfires: The Great Outdoors
See event details | WFCU Centre
Celebrate the outdoors at the 4th Annual Great Outdoors Night as the Windsor Spitfires take on the Sudbury Wolves! Whether you love camping, fishing, hunting, or exploring nature, this themed game night offers outdoor-inspired activities, family-friendly fun, and exciting hockey action.

🥊 October 16 – Owen Sound Attack vs. Windsor Spitfires: Fight Night
See event details | WFCU Centre
Get ready for an action-packed night of hockey as the Windsor Spitfires face off against the Owen Sound Attack for Fight Night! Fans can enjoy an exciting matchup featuring fast-paced hockey and plenty of game-night energy.

🏒 October 17 – Windsor Lancers Hockey vs. Western
7:30 PM | Adie Knox Herman Arena
Get ready for an exciting night of university hockey as the Windsor Lancers take on Western! Cheer on the Lancers as they hit the ice for an action-packed matchup filled with competitive play, team spirit, and plenty of excitement.

🎳 October 17 – Forest Glade Optimist Junior Bowling
See event details | SuperBowl Lanes
Give young bowlers the chance to learn, play, and make new friends at Forest Glade Optimist Junior Bowling! This children’s bowling league helps participants develop their bowling skills, build confidence, and enjoy a fun, welcoming environment.

That's your week across Windsor-Essex. Whether you're catching Dear Evan Hansen at the Capitol, exploring the Kingsville Migration Festival, or dressing up for the Diablerie Vampire Ball, there's plenty to fill your calendar before Halloween creeps closer. Get out there, support local — we'll be back next week with another roundup of the region's best.
— Windsor Pulse