This weekend · Windsor, ON · 27 events

Things to do in Windsor this weekend

Friday, October 16 to Sunday, October 18 · 27 events

27 events are listed in Windsor, Ontario for this weekend (Oct 16–18), soonest first. The most common categories are arts & culture (5), live music (5) and community (4). None of the events listed are marked free.

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By vibe

Friday, October 16

  1. Chalk Pastel Country Landscape Class for Adults and Teens

    Chalk Pastel Country Landscape Class for Adults and Teens

    3919 Howard Avenue,Windsor,N9G 1N9,CA

    Check price

  2. Learn how to Paint with Watercolors, Adults and Teens Classes

    Learn how to Paint with Watercolors, Adults and Teens Classes

    Expressive Brush Art Studio

    Check price

  3. Disco & Villians Present: The 10th Annual Rocky Horror Screening & Drag Show (Disco’s 10th Rocky)

    Disco & Villians Present: The 10th Annual Rocky Horror Screening & Drag Show (Disco’s 10th Rocky)

    VillainsBeastro Windsor

    Check price

  4. Big Tree Acrylic Painting Class for Adults and Teens

    Big Tree Acrylic Painting Class for Adults and Teens

    Expressive Brush Art Studio

    Check price

  5. Sound Bath by Candlelight Wyandotte

    Sound Bath by Candlelight Wyandotte

    Downriver Council For the Arts

    Check price

  6. Freaks Come Out At Night (1st Official Halloween Party)

    Freaks Come Out At Night (1st Official Halloween Party)

    More Life Lounge

    Check price

  7. PERREOLAND | DETROIT

    PERREOLAND | DETROIT

    Russell Industrial Center | Exhibition Center

    Check price

Saturday, October 17

  1. Friday Comedy Session LIVE At Tipsy Toucan (Oct 16th)

    Friday Comedy Session LIVE At Tipsy Toucan (Oct 16th)

    The Tipsy Toucan

    CA$15.00

  2. Black Men's Wellness Day - Detroit - 2026

    Black Men's Wellness Day - Detroit - 2026

    Renaissance High School

    Check price

  3. 2026 NID-HCA Housing Help Center "Free" Homebuyer Education Workshops

    2026 NID-HCA Housing Help Center "Free" Homebuyer Education Workshops

    8201 Vernor W

    Check price

  4. Windsor-Essex Winter-Ready Home Show 2026

    Windsor-Essex Winter-Ready Home Show 2026

    THE WFCU CENTRE

    Check price

  5. The ReVamp Clothing Swap Festival - Fall 2026

    The ReVamp Clothing Swap Festival - Fall 2026

    Chandler Park Fieldhouse

    Check price

  6. FCA Afternoon in the Parlour

    FCA Afternoon in the Parlour

    3200 Woodland Drive, Windsor, ON, Canada, Ontario N9E 1Z5

    Check price

  7. HALLOWCRAWL 2026 - Royal Oak

    HALLOWCRAWL 2026 - Royal Oak

    Royal Oak

    Check price

  8. Third Annual Grosse Pointe Witches Ride

    Third Annual Grosse Pointe Witches Ride

    High Pointe Burger Jointe

    Check price

  9. Clay Rose, Art Class for Teens and Adults

    Clay Rose, Art Class for Teens and Adults

    Expressive Brush Art Studio

    Check price

  10. HABLA DETROIT: SPANISH SPEAKING MIXER

    HABLA DETROIT: SPANISH SPEAKING MIXER

    3400 Bagley St

    Check price

  11. Ghost Ship

    Ghost Ship

    78 Riverside Dr W, Windsor, ON, Canada, Ontario N9A 2S4

    Check price

  12. STAND UP COMEDY SHOW

    STAND UP COMEDY SHOW

    Meteor

    CA$6.85

  13. Potters Wheel Classes for Adults and Kids 8 years and older

    Potters Wheel Classes for Adults and Kids 8 years and older

    Expressive Brush Art Studio

    Check price

  14. Champion Sound - A Night In South Africa

    Champion Sound - A Night In South Africa

    Northern Lights Lounge

    Check price

Sunday, October 18

  1. Ben Albert: Live in Windsor - 8PM Show

    Ben Albert: Live in Windsor - 8PM Show

    The Tipsy Toucan - Public House

    Check price

  2. Diablerie Vampire Ball

    Diablerie Vampire Ball

    Water's Edge Event Centre

    Check price

  3. Spooky Spider Web Craft Workshop – Halloween Art for Kids & Families

    Spooky Spider Web Craft Workshop – Halloween Art for Kids & Families

    Expressive Brush Art Studio

    CA$27.45

  4. Drizzy Bowl: Drake Night - Drake Hits & Tribute (All Night)

    Drizzy Bowl: Drake Night - Drake Hits & Tribute (All Night)

    Orchid Theatre

    Check price

  5. The Black Keys | Official Caesars Ticket + Hotel Packages

    The Black Keys | Official Caesars Ticket + Hotel Packages

    The Colosseum at Caesars Windsor

    Check price

  6. The Black Keys: PEACHES 'N KREAM

    The Black Keys: PEACHES 'N KREAM

    The Colosseum at Caesars Windsor

    Check price

Questions about Windsor this weekend

What's on in Windsor this weekend?
27 events are listed in Windsor for this weekend (Oct 16–18), including Chalk Pastel Country Landscape Class for Adults and Teens, Learn how to Paint with Watercolors, Adults and Teens Classes and Disco & Villians Present: The 10th Annual Rocky Horror Screening & Drag Show (Disco’s 10th Rocky).
Are there free events in Windsor this weekend?
None of the 27 events listed for this weekend (Oct 16–18) are marked free. Free listings appear when a source says admission is free.
When is the next evntally digest?
The next weekly Windsor digest goes out Thursday October 15, with five picks matched to your taste. The first two digests are free with no card; continue for CA$2.99/mo only if you choose.

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Five Windsor picks in your inbox every Thursday. Matched to your taste. Ticket links included.

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Two Thursday digests free. No card. Continue for CA$2.99/mo only if you choose. Tickets cost extra.