Friday Five: Celebrate the Holidays in Downtown Oakville

With its charming streetscape, historic buildings and lakeside location, Downtown Oakville is the perfect place to experience the magic of the Christmas season. Here are five things to see and do in Downtown Oakville over the holidays:

Tree Lighting Ceremony & Holiday Market (November 15) 
For many Oakville residents, Downtown Oakville’s annual Tree Lighting Ceremony & Holiday Market is the official start of the holiday season. Taking place on Friday, November 15 from 7-9 p.m. in Centennial Square, this year’s event will feature live music, shopping, beer, coffee, food and photo ops. Click here for the full vendor list.

Santa Claus Parade (November 16) 
Santa Claus is coming to town – Downtown Oakville, that is. A newly reopened Lakeshore Road means Santa can make his way across Lakeshore Road East for the annual Santa Claus Parade on November 16. Grab a hot beverage or a treat from your favourite cafe, watch the parade, then get a head start on your holiday shopping. The parade starts at 9 a.m. at Reynolds and Lakeshore, so be sure to arrive early to get a prime spot. Click here for full event details.

Illuminated Ornament in Towne Square
Capture your holiday memories with a photo in front of our new illuminated ornament, which will sit in Centennial Square from November 10 until early January. This 10-foot art installation also has seating, so you can rest and enjoy a coffee or hot chocolate during your holiday shopping.

Christmas Cheer (every weekend from November 30-December 14) 
We’re adding a little festive flair to your holiday shopping with weekend activations taking place from November 30 to December 14, including wagon rides, carolers, holiday decor and more.

Newly Opened Street for Your Holiday Shopping
After eight months of construction, Lakeshore Road East between Navy and Dunn Streets is scheduled to reopen to vehicle traffic by mid-November – just in time for the holidays! While some elements like granite curbs and lamp posts won’t be in place in some areas, the Town of Oakville has advised that the road will be fully accessible to vehicles and pedestrians. Click here for a directory of stores so you can start planning your holiday shopping trip.

  • Featured Events

    Fri 22

    Customer Appreciation Night @ Dove + Arrow

    November 22
    Oakville Ontario
    Canada
    Sat 23

    The Frogs Are Back in Town Exhibit @ Towne Square Gallery

    November 23 @ 12:00 pm - 4:00 pm
    Oakville Ontario
    Canada
    Sat 23

    Eat Drink & Be Merry at Churchill Place Retirement Residence

    November 23 @ 1:00 pm - 4:00 pm
    Oakville Ontario
    Canada
    Tue 26

    Black Friday Sale at Creo Wear Couture

    November 26 @ 9:00 am - 5:00 pm
    Oakville Ontario
    Canada
    Wed 27

    Holiday Fest @ Abaton Integrative Medicine

    November 27 @ 10:00 am - 11:00 am
    Oakville Ontario
    Canada
  • P Parking