- November 15 – December 23: Toronto Christmas Market
- December 1: Rotary’s Maple Leaf Trivia
- December 1: Santa and Mrs. Clause in the Market
- December 1: Waterdown Made For You Market
- December 1: Waterdown Shop the Village Holiday Kickoff
- December 1: Santa Shuffle Fun Run & Elf Walk
- December 1 -2, 8-9, 15-16: Downtown Oakville Christmas Cheer
- December 2: Brunch with Santa at African Lion Safari
- December 3: Big Brothers, Big Sisters Shop For Kids Sake Online Auction
- December 4: Christmas in the Pioneer Spirit
- December 4-9: Victorian Christmas at Dundurn Castle
- December 5: 8th Annual Wellness Expo
- December 6: Holiday Craft at Waterdown Library
- December 7: Barton Street Christmas Market
- December 7: The Nutcracker Ballet Theatre of Odessa
- December 8: CHCH Burlington Santa 5KM Race
- December 8: Stuff the Bus Food Drive
- December 9: Symphony on the Bay – Christmas Delights
- December 14: James Street North Art Crawl
- December 15: Pet Pics with Santa
- December 22: Twas the Night Before Christmas at Westfield Heritage Village
- December 27-30: Victorian Christmas at Bronte Creek
- December 31: New Years Eve at Bronte Creek
- December 31: Coyote Howl Hike