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Step into the Magic: Downtown Oakville's Hometown Holiday Extravaganza

Updated: Nov 17, 2023

The most enchanting time of the year is upon us, and Downtown Oakville is thrilled to announce the return of the beloved Hometown Holiday celebration, sponsored by American Express Canada. From November 17 through January 6, our historic commercial district becomes a festive paradise where the season's spirit sparkles on every corner.

Light Up the Night – November 17

Kickstart the season at our 'Light up the Night' event from 5 PM to 9 PM. Downtown Oakville will come alive with the first magical flicker of our 30-foot natural tree in Towne Square, officially lighting up at 5:30 PM. Surrounding the splendour of the tree lighting, The Sugar Plums are back from NYC with four enchanting performances.

Stroll over to Centennial Square and bask in our Winter Wonderland of lights, where the festive melodies of the Candy Cane Carollers will fill the air. And while you're there, remember to visit Santa at his Cozy Cottage. Next, delight in holiday window displays and get a head start on your holiday shopping as participating shops stay open late or catch a romantic horse and carriage ride through Downtown Oakville's historic district.

Rock'n Around | Silent Holiday Disco - November 25

Presented in partnership with Sotheby's International Realty Canada, join us on November 25 for a Holiday Silent Disco that promises to get you 'Rock'n Around' the Christmas tree. This Silent Disco night will have you moving to the beat of Christmas classics under the glow of festive lights. Remember to reserve your headset for a 60-minute session packed with dancing and holiday happiness.

Sips, Selfies, and Santa

On select dates, warm up with free hot cocoa from our vintage airstream in Towne Square and capture the moment with an Instagram-worthy photo. Meet the jolly man himself in his Cozy Cottage and enjoy the holiday stylings of The Candy Cane Carollers, The MacGregor Carollers, Ellen Daly, Natasha Meister, and Gareth Bush.

Discover, shop, eat, and celebrate in Downtown Oakville; it's the best part of your holiday!

For a complete list of Hometown Holiday festivities, check out our Hometown Holiday page and peek at our Community Calendar, where other festive opportunities await. Let's make this holiday season one to remember together in Downtown Oakville.

Thank you to our Sponsor, American Express Canada.

Through Shop Small®, the Amex community comes together to support the everyday small businesses we can’t live without.


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