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Festivals & Events

Winter Wonderland

Saturday, December 6 & 13
11:30 am – 3:00 pm
Millennium Square

Join the City of Pickering and Nautical Village businesses for an exciting event in Millennium Square this Winter! Enjoy an opening day live ice carving, select holiday vendors, winter character performers, buskers, s’mores stations, and miniature train rides through Nautical Village.

Vendor Callouts

Are you a farmer, artisan, crafts vendor, food vendor, apparel vendor, flower vendor, or community group? Apply to be considered for our annual Winter Wonderland event this December! 

The registration deadline is Friday, October 31, 2025. All successful applicants will be informed by Friday, November 7, 2025, at the latest. Space is extremely limited.
This application form can be submitted online. To apply by mail, print the application and send to:

Winter Wonderland
Community Services
City of Pickering
One The Esplanade Pickering, ON L1V 6K7

Performer Callouts

Interested in performing at Fall Fling or Winter Wonderland? Please email events@pickering.ca

Include your:

  • Name
  • Link to performance examples
  • Social media handles

Applications close:

  • Fall Fling - September 30th at 4:30 pm
  • Winter Wonderland - October 31st at 4:30 pm

Ice Sculpture

Performers

Miniature Train

S'mores

Winter Decor

Photos and video may be recorded at this event by designated City photographers & videographers. These materials may be used in future City of Pickering education, advertising, and other internal/external promotions, without compensation.

Any questions related to the collection of this information should be directed to the City Clerk, One the Esplanade, Pickering, ON L1V 6K7, 905.420.4611.

For the safety of all attendees, we encourage any dogs that do not do well with people, crowds, loud noises, or other dogs to be left at home.

Please note, all dogs entering any City event must comply with the Responsible Pet Ownership By-law (6811/07) and the Dog Owners Liability Act.

Dogs that have characteristics similar to a Pit Bull (under the act) must wear a muzzle.

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Contact Us

Community Services
One The Esplanade
Pickering, Ontario
Canada L1V 6K7

905.420.4620

Email Community Services

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