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Discover Downtown Oakville's outdoor shopping experience, your festive destination where history and modern charm collide. Explore historical buildings and trendy boutique shops while enjoying international cuisine. Take in the charming store displays and the spectacular Winter Wonderland of Lights. And don't miss these hometown holiday events for a guaranteed festive season!

Holiday Happenings 

  • Shop the Street - Sidewalk Sale
    Shop the Street - Sidewalk Sale
    Thu, Jun 13
    Downtown Oakville
    Jun 13, 2024, 10:00 a.m. – Jun 16, 2024, 6:00 p.m.
    Downtown Oakville, 166 Lakeshore Rd E, Oakville, ON L6J 1H6, Canada
    Head Downtown and get ready for summer with savings from Downtown Oakville merchants. Shop the Street for deals along the sidewalk and in-store.
  • ART REACH
    ART REACH
    Thu, Jun 13
    Knox Presbyterian Church Oakville
    Jun 13, 2024, 7:00 p.m. – 10:00 p.m.
    Knox Presbyterian Church Oakville, 1173 North Service Rd E, Oakville, ON L6H 1A7, Canada
    Purchase a ticket for a special evening and be guaranteed to go home with an original painting by renowned Oakville artist David Peacock.
  • Thursday Soiree
    Thursday Soiree
    Multiple Dates
    Thu, Jun 13
    Beacon
    Jun 13, 2024, 7:00 p.m. – 11:00 p.m.
    Beacon, 305 Lakeshore Rd E, Oakville, ON L6J 1J3, Canada
    Join us tonight for our Thursday Soiree, every Thursday, only at Beacon. Featuring live DJ & $15 cocktails
  • Town Of Oakville Bike Month Events
    Town Of Oakville Bike Month Events
    Multiple Dates
    Sat, Jun 15
    Oakville
    Jun 15, 2024, 1:00 a.m. – 4:30 a.m.
    Oakville, Oakville, ON, Canada
    Join us in celebrating bike month Oakville Downtown at our decorate your bike event, bike history work shop, and bike repair work shop
  • Summer Sweat Fitness Series | SPINCO
    Summer Sweat Fitness Series | SPINCO
    Multiple Dates
    Sat, Jun 15
    Towne Square
    Jun 15, 2024, 9:00 a.m. – 2:00 p.m.
    Towne Square, Towne Square, Oakville
  • Summer Sweat Fitness Series  Hot Yoga & Pilates
    Summer Sweat Fitness Series  Hot Yoga & Pilates
    Multiple Dates
    Sat, Jun 15
    Towne Square
    Jun 15, 2024, 9:00 a.m. – 9:45 a.m.
    Towne Square, Towne Square, Oakville
    Enjoy a complimentary HOT HIIT Pilates class in the beautiful Downtown Oakville as we celebrate the Summer Sweat Series! Bring your yoga mat, towel and bottle of water, along with your friends and family! Everyone is welcome
  • Father's Day Free Ride
    Father's Day Free Ride
    Multiple Dates
    Sun, Jun 16
    Flyspin
    Jun 16, 2024, 8:00 a.m. – 9:00 a.m.
    Flyspin, 302 Lakeshore Rd E, Oakville, ON L6J 1J2, Canada
    Celebrate Father’s Day with a special free ride at Flyspin! Join us for an exhilarating 45-minutes spin class designed for dads and their kids.
  • Dads Ride for Free!
    Dads Ride for Free!
    Sun, Jun 16
    SPINCO Oakville
    Jun 16, 2024, 8:00 a.m. – 1:00 p.m.
    SPINCO Oakville, 229 Lakeshore Rd E, Oakville, ON L6J 1H7, Canada
    Dads ride for free for classes on June 16th. Email infooakville@spinco.ca to reserve your spot.
  • Oakville Speed Dating (Ages 28-40)
    Oakville Speed Dating (Ages 28-40)
    Multiple Dates
    Tue, Jun 18
    Figaro Coffee House
    Jun 18, 2024, 7:00 p.m. – 11:00 p.m.
    Figaro Coffee House, 350 Lakeshore Rd E, Oakville, ON L6J 1J6, Canada
    Go on fun, fast dates and meet up to 15 new people in one fun night!
  • Oakville Film Festival: Honey I Shrunk the Kids Launch Event
    Oakville Film Festival: Honey I Shrunk the Kids Launch Event
    Wed, Jun 19
    Downtown Oakville Town Square
    Jun 19, 2024, 6:00 p.m. – 11:00 p.m.
    Downtown Oakville Town Square , Oakville, ON L6J, Canada
    Join us for a fantastic evening at the free Family-Friendly Launch Event in Towne Square, Oakville, on Wednesday, 19th June from 6 pm to 11 pm. The highlight of the evening will be an outdoor screening of the beloved family comedy, "Honey I Shrunk the Kids," starting at 9 pm. Bring your lawn chairs
  • Fun Run
    Fun Run
    Multiple Dates
    Wed, Jun 19
    Running Room
    Jun 19, 2024, 6:00 p.m. – 7:00 p.m.
    Running Room, 156 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Join the Running room every Wednesday at 6PM for a fun free social group run!
  • Cooking Class - Ravioli
    Cooking Class - Ravioli
    Thu, Jun 20
    Mercato Sociale
    Jun 20, 2024, 6:30 p.m. – 9:00 p.m.
    Mercato Sociale, 257 Lakeshore Rd E, Oakville, ON L6J 1H9, Canada
    Pasta Making with Chef Enzo Campisi - Ravioli ~ Thursday June 20th 2024 6:30pm-9:00pm
  • Singles Mingle - SPIN CLASS
    Singles Mingle - SPIN CLASS
    Thu, Jun 20
    FlySpin
    Jun 20, 2024, 6:30 p.m. – 7:30 p.m.
    FlySpin, 302 Lakeshore Rd E, Oakville, ON L6J 1J2, Canada
    Join our inaugural Downtown Oakville Singles Mingle event. See if sparks fly at an exhilarating class at FLYSPIN, then unwind and connect overdrinks in their coffee lounge.
  • Oakville Film Festival: The Canadian Premiere Kipkemboi
    Oakville Film Festival: The Canadian Premiere Kipkemboi
    Thu, Jun 20
    Oakville Centre for the Performing Arts
    Jun 20, 2024, 7:30 p.m.
    Oakville Centre for the Performing Arts, 130 Navy St, Oakville, ON L6J 2Z4, Canada
    Experience a night of cinematic brilliance at the EY Gala. Join us for the Canadian Premiere of "Kipkemboi," an inspiring film directed by Charles Uwagbai. This Kenya/Canada co-production follows the journey of a teenage African math prodigy who shakes the global financial markets.
  • Anniversary Event
    Anniversary Event
    Fri, Jun 21
    Amore Skin and Wellness Center
    Jun 21, 2024, 3:00 p.m. – 7:00 p.m.
    Amore Skin and Wellness Center, 83 Reynolds St, Oakville, ON L6J 3K3, Canada
    Join us for a spectacular celebration of our anniversary! We are thrilled to invite both our valued current clients and new friends to an unforgettable event filled with excitement, enjoyment, and appreciation.
  •  International Yoga Day: Deep Stretch & Soundbath
     International Yoga Day: Deep Stretch & Soundbath
    Fri, Jun 21
    HOT Yoga & Pilates
    Jun 21, 2024, 7:00 p.m. – 8:30 p.m.
    HOT Yoga & Pilates, 178 Lakeshore Rd E, Oakville, ON L6J 1H6, Canada
    Join us for a soothing Deep Stretch Yoga class with a mesmerizing Sound Bath in celebration of International Yoga Day!
  • Oakville Film Festival: GALA For National Indigenous Peoples Day The Great Salish Heist !
    Oakville Film Festival: GALA For National Indigenous Peoples Day The Great Salish Heist !
    Fri, Jun 21
    Oakville Centre for the Performing Arts
    Jun 21, 2024, 7:30 p.m.
    Oakville Centre for the Performing Arts, 130 Navy St, Oakville, ON L6J 2Z4, Canada
    Celebrate National Indigenous Peoples Day at the OFFA Gala on Friday, 21st June at 7:30 pm, held at the Oakville Centre for the Performing Arts. This event features the Eastern Canadian Premiere of "The Great Salish Heist," a unique Indigenous comedy about a First Nations Archaeologist and his crew
  • Oakville Galleries Summer Exhibitions and Outdoor Film Program
    Oakville Galleries Summer Exhibitions and Outdoor Film Program
    Multiple Dates
    Sat, Jun 22
    Oakville Galleries
    Jun 22, 2024, 10:00 a.m. – 5:00 p.m.
    Oakville Galleries, 120 Navy St, Oakville, ON L6J 2Z4, Canada
    Oakville Galleries is excited to announce its summer 2024 exhibitions Rogue Planet by German artist duo Hedda Roman
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