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  • Tim Swaddling & his Evil Elixirs wsg/The Tipsy Two & Whoa Nellie! plus Claudia Rae & her 6 String Guitar: Live

    Villains Beastro 256 Pelisier st, Windsor, Ontario, Canada

    One Sinister Night Only • Four Acts Of Terror In A Single Show • High Value Programme Saturday, October 18th, 2025 8.30PM (early start!) • $10 / PWYC cover • Arrive early for best seating Tim Swaddling & The Iron Horses (postmodern abstract expressionist blues-folk-rock) The Tipsy Two (outlaw country punkabilly upstart rooster jazz) Whoa...

  • Cherry Garcia Band at The Cherry Rock Lounge

    The Cherry Rock Lounge 63 Pitt St E, Windsor, Ontario, Canada

    Cherry Garcia Band back in Windsor at The Cherry Rock Lounge! get yer dancing shoes on y’all, we will be jamming Grateful Dead, Jerry Garcia, Motown, Dylan, Reggae, originals. live visuals by the amazing Hermetic Light Show! doors 9pm, music 10pm

  • Average Joe’s “Crooked Swagger Live”

    Average Joe's Sports Bar 1286 Lauzon Road, Windsor, Ontario, Canada

    Crooked swagger will be Rocking Average Joe's !!! Saturday October 18th come join us !! Great Food , Great People , Great place for Live music !!

  • Fall Wellness Fair

    Unity Spiritual Centre of Windsor 3640 Wells St, Windsor, Ontario, Canada

    Explore our exhibit hall brimming with holistic treasures—from crystals and herbal remedies to energy tools and conscious living products. Then, wander over to the healing villa, where gifted practitioners offer a variety of restorative modalities to elevate your mind, body, and spirit.

  • Detroit Free Press International Marathon

    The City of Windsor is gearing up to join in the excitement of the Detroit International Free Press Marathon! One of the few truly international marathon courses in the world, the event attracts racers from across the globe. The racecourse showcases iconic and historic neighbourhoods in Detroit and includes crossings between Canada and the US...

  • Mirror in the Attic – an original Cirque-style experience

    Masonic Temple Ballroom 986 Ouellette Ave, Windsor, Ontario, Canada

    Mirror in the Attic – an original Cirque-style experience One Show Only! With special guest opening performances! Sunday October 19th, 2pm At the Temple Ballroom, 986 Ouellette Avenue Tickets $25 available at https://bloomsburyhouse.org/ written by Bill Nuvo with Alex Urbano & Melissa Arditti Join a magical and memorable journey into another realm! On a stormy...

  • Music Bingo Trivia

    Walkerville Brewery 525 Argyle Rd, Windsor, Ontario, Canada

    Join us for Music Bingo Trivia Sunday, October 19th at 5pm with your host Mack Flash Entertainment. A night filled with a little bit of bingo, a little bit of trivia and a whole lot of music! Music Bingo Trivia is always free to play and great prizes to be won! Participation is first come,...

  • Kaleb Hikele

    Phog Lounge 157 University Ave W, Windsor, Ontario, Canada

    Live in Windsor for one night only at Phog Lounge. Kaleb Hikele's 'Storytelling' Tour is the debut of a new solo album, performed live on stage from front to back. With special guests The Indiana Drones (Acoustic) and more. Admission at the door, open 7pm.

  • The Music of Star Wars

    Capitol Theatre Windsor 121 University Ave W, Windsor, Ontario, Canada

    The Music of Star Wars will transport you into that iconic galaxy far, far away. The WSO brings the thrilling music from the great John Williams‘ legendary scores to life. During the program Maestro Franz will interact with the audience, asking you to Name That Tune. This concert is 120 minutes, with an intermission.

  • Small Business Summit

    St. Clair Centre for the Arts 201 Riverside Drive West, Windsor, Ontario, Canada

    This half-day experience is tailored for entrepreneurs and small business owners who want to elevate their business through knowledge, strategy and community. $95 +HST Hosted in partnership with Small Business & Entrepreneurship Centre and Windsor Essex Chamber of Commerce.

  • Ottawa 67’s vs. Windsor Spitfires

    WFCU Centre 8787 McHugh St., Windsor, Ontario, Canada

    Enjoy thrilling OHL action as your Windsor Spitfires are set to face off the Ottawa 67’s! Puck drops at 7:05pm. This game’s theme is: The Great Outdoors Night Celebrate nature, adventure, and everything outdoorsy. Plus, the first 1,000 fans receive a limited-edition player poster! Giveaway: Player Poster

  • House of Hades – Charity Halloween Costume Gala

    The Windsor Club 2072 Riverside Dr E, Windsor, Ontario, Canada

    Take a trip with us down below to the Greek Underworld 😈 House of Hades is our most anticipated event of the year! Sponsored By: LIUNA 625, Sterling Ridge Group, Superbowl Lanes, Mastro Kitchen Studio, St. Clair College Alumni Association & more! Join the Fight Like Mason Foundation for an incredible costume gala like no...

  • Rat Race Tour

    Phog Lounge 157 University Ave W, Windsor, Ontario, Canada

    Fri, 24 Oct, 2025 at 07:00 pm to 11:00 pm (EDT) SHIPRAT live in Windsor! Tickets coming soon. Doors @ 7 Bands @ 8 19+ We do not tolerate sexism, racism, homophobia, transphobia, or any other kind of hate. This event is NOTAFLOF (No One Turned Away For Lack of Funds). If you need accommodations,...

  • WIFF: Windsor International Film Festival – October 25th Screenings

    Capitol Theatre Windsor 121 University Ave W, Windsor, Ontario, Canada

    With over 200 films at WIFF 2025, there truly is something for everyone! Discover the full list of movies here, or dive into our program book. Can’t decide on what to see? Reach out to our team on social, and we’d be happy to provide some recommendations. The Windsor International Film Festival (WIFF) is Canada’s...

  • WYCked Run/Walk 5K – Halloween Fun for a Cause!

    Saturday, October 25, 2025 Registration: 9:30 AM | Run/Walk Start: 10:00 AM Ambassador Park Trail – Windsor Riverfront Tickets: $25 – Register at: https://bit.ly/46ZUqXu Celebrate Halloween and support local youth at the WYCked Run/Walk 5K, a family-friendly event benefiting the Windsor Youth Centre (WYC), a vital program of The Downtown Mission. Dress up, bring your...

  • Run for Windsor 1 -5 KM

    Malden Park 4200 Malden Road, Windsor, Ontario, Canada

    Every dollar raised goes directly toward enhancing care at Windsor Regional Hospital, ensuring that our efforts have a meaningful impact close to home. With the help of participants, volunteers, and sponsors, we strive to create an event that is memorable and inspires long-term change, bringing people together in the spirit of health, unity, and giving.

  • Sarah McLachlan

    Caesars Windsor 377 Riverside Drive East, Windsor, Ontario, Canada

    7:30 PM - The music of Sarah McLachlan brings the Fumbling Towards Ecstasy 30th Anniversary 2025 Canadian Tour. The tour hits Caesars Windsor with special guest Tiny Habits.

  • A Girls Night Out in Handbag Heaven – Handbags for Housing

    Giovanni Caboto Club 2175 Parent Avenue, Windsor, Ontario, Canada

    Join us for the ultimate girls’ night out at Handbags for Housing, an unforgettable evening of fashion, fun, and philanthropy in support of Habitat for Humanity Windsor-Essex. This high-energy event brings together hundreds of guests for an exciting night featuring a gourmet meal, live music, a fabulous candy buffet, and our signature purse auction featuring...

  • NIGHT OF THE LIVING TRANSANITY: Drag Show and Halloween Party

    Walkerville Brewery 525 Argyle Rd, Windsor, Ontario, Canada

    Save the date and get your tickets for our upcoming fundraiser!! 🤩 The House of Cures presents NIGHT OF THE LIVING TRANSANITY – Drag Show & Halloween Party! Saturday November 1st, 8:00pm – 10:30pm, Doors at 7:30pm at the Walkerville Brewery, 525 Argyle Rd, Windsor ON “One Night Only” – Join your hosts from the...

  • My Letter to Santa Holiday Market

    Come out and support small local businesses while finding that unique gift for that special someone. Food for purchase on site. Santa will be there from 12:00 to 2:00 pm Free Admission