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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 

  • Winter Wonderland of Lights
    Winter Wonderland of Lights
    Fri, Nov 17
    Centennial Square (Lakeshore/Navy)
    Nov 17, 2023, 7:00 p.m. – Jan 08, 2024, 7:00 p.m.
    Centennial Square (Lakeshore/Navy), 120 Navy St, Oakville, ON L6J 2Z4, Canada
    Take in the wonder of the season at our Winter Wonderland of Lights. Displays throughout Downtown from Towne Square to Centennial Square (Navy/Lakeshore).
  • Free Hot Cocoa and Fire Pits
    Free Hot Cocoa and Fire Pits
    Multiple Dates
    Sat, Dec 09
    Towne Square
    Dec 09, 2023, 2:00 p.m. – Dec 10, 2023, 6:00 p.m.
    Towne Square , 166 Lakeshore Rd E, Oakville, ON L6J 1H6, Canada
    Stop by our vintage airstream in Towne Square to pick up a free hot cocoa, warm up by our fire pits and enjoy our Winter Wonderland of Lights.
  • Visit with Santa
    Visit with Santa
    Multiple Dates
    Sat, Dec 09
    Centennial Square
    Dec 09, 2023, 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 - Natasha Meister
    Live Holiday Music - Natasha Meister
    Multiple Dates
    Sat, Dec 09
    Towne Square
    Dec 09, 2023, 2:00 p.m. – 6:00 p.m.
    Towne Square, Oakville, ON L6J, Canada
    Enjoy music during Light up the Night and the first 3 weekends in December.
  • Horse and Carriage Rides
    Horse and Carriage Rides
    Multiple Dates
    Sun, Dec 10
    Towne Square - Pick Up at Robinson St.
    Dec 10, 2023, 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. Reservation Required. Reservation is valid for one ride, for up to 4 people. Please only reserve one time block.
  • Window Wonderland
    Window Wonderland
    November 17 - December 31
    Oakville Downtown
    November 17 - December 31
    Oakville Downtown , 146 Lakeshore Rd E, Oakville, ON L6J 1H4, Canada
    Vote for your favourite window for your chance to win a $250 Downtown Oakville Gift Card.
  • In-Store Special Offers
    In-Store Special Offers
    Holiday Offers
    Downtown Oakville
    Holiday Offers
    Downtown Oakville, Lakeshore Road East
    Check out all the amazing in-store offers just in time for the holidays.
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