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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 

  • Light up the Night
    Light up the Night
    Fri, Nov 15
    Towne Square
    Nov 15, 2024, 5:00 p.m. – 10:00 p.m.
    Towne Square, Oakville, ON, Canada
    Join us for the kick-off to Downtown Oakville's Hometown Holiday as we light up the night.
  • Rock'n Around - Silent Holiday Disco
    Rock'n Around - Silent Holiday Disco
    Sat, Nov 23
    Towne Square
    Nov 23, 2024, 5:00 p.m. – 10:00 p.m.
    Towne Square, Oakville, ON L6J, Canada
    Back with a beat, this Silent Disco night is all about grooving and moving under our twinkly festive tree lights!. Rock out at a 60-minute session filled with iconic Christmas tunes, dancing, and pure holiday joy.
  • Visit with Santa
    Visit with Santa
    Multiple Dates
    Sat, Nov 30
    Centennial Square
    Nov 30, 2024, 2:00 p.m. – 6:00 p.m.
    Centennial Square , 120 Navy St, Oakville, ON L6J 2Z4, Canada
    Meet Santa in his Cozy Cottage in Centennial Square (Navy/Lakeshore). From 2-3PM Santa will walk the streets of Downtown Oakville before settling in at his cottage. Don't forget your camera!
  • Live Holiday Music  - The Candy Cane Carollers
    Live Holiday Music  - The Candy Cane Carollers
    Multiple Dates
    Sat, Nov 30
    Towne Square
    Nov 30, 2024, 3:00 p.m. – 5:00 p.m.
    Towne Square, Oakville, ON L6J, Canada
    The Candy Cane Carolers , Toronto's premier holiday entertainers, bring their beautiful a capella holiday music to Downtown.
  • Sip, Shop & Celebrate
    Sip, Shop & Celebrate
    Sat, Nov 30
    Downtown Oakville
    Nov 30, 2024, 4:00 p.m. – 8:00 p.m.
    Downtown Oakville, 146 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Join us for a festive girls' night out! George Street transforms into a holiday market, plus, purchase a ticket for just $10 to enjoy sampling from participating boutiques. Ticket holders will receive a free souvenir travel glass to use as you sip your way through downtown.
  • Visit with Santa
    Visit with Santa
    Multiple Dates
    Sat, Dec 07
    Centennial Square
    Dec 07, 2024, 2:00 p.m. – 6:00 p.m.
    Centennial Square , 120 Navy St, Oakville, ON L6J 2Z4, Canada
    Meet Santa in his Cozy Cottage in Centennial Square (Navy/Lakeshore). From 2-3PM Santa will walk the streets of Downtown Oakville before settling in at his cottage. Don't forget your camera!
  • Horse and Carriage Rides
    Horse and Carriage Rides
    Multiple Dates
    Sun, Dec 08
    Towne Square - Pick Up at Robinson St.
    Dec 08, 2024, 2:00 p.m. – 6:00 p.m.
    Towne Square - Pick Up at Robinson St., Oakville, ON L6J, Canada
    Enjoy a horse and carriage ride around the historic Downtown Oakville neighbourhood.
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