As the holiday season approaches, get ready for this season’s TOP events that will make your spirits bright! In YDH there are an array of festive gatherings, enchanting experiences, and joyful celebrations lined up to make this season truly unforgettable. From enchanting light displays to heartwarming community events, there’s something for everyone to enjoy. So, mark your calendars and get ready for a season of merriment and togetherness.
York



Canada’s Wonderland Winterfest
Select nights, November 21, 2026 – January 3, 2027
Willow Wonderland: Holiday Market – TBD
November 15 & 16, 2025
Markham Home for the Holidays
November 20, 21 & 22, 2026
Richmond Hill Merry Marketplace
Saturdays- November 14, 21, 28, December 5, 12, 2026
Niemi’s Christmas Market & GnomeVille
Every Friday & Saturday, November 13 – December 19, 2026
Magical Christmas Forest
November 27 – 29, December 3 – 6, 9 – 13, 16 – 23, 2026
Holiday Performances at Flato Markham Theatre
Multiple dates in November & December 2026
Aurora’s Christmas Market
November 27 – November 29, December 4 – December 6, 2026
Stouffville Holiday Market
November 20 – 21, 2026
Kingscraft Studio Sale
November 13 – 15 & 20 – 22, 2026
The Village at Black Creek Santa and Festive Nights Experiences
Weekends in December 2026
Newmarket Frozen Friday
December 4, 2026
Torch Lit Hikes at Sibbald Point Provincial Park -TBD
December through February
Durham

A Country Path Christmas – Various Locations in Clarington
Mid November until December 23, 2026 – various hours
Pick up a Holiday postcard at any of the participating ACP locations and get it stamped/stickered for a chance to win a gift basket valued at over $200.
Oshawa Holiday Experience -TBD
Various dates in November & December
Winter Fest Vendor Market
November 21 and 22, 2026
Applewood Farm and Winery Holiday Market
Sunday, November 29, 2026
Christmas in the Village Brooklin
November 21, 2026
Holiday in the Hills at Orono Fairgrounds
Gates open Saturday November 21, 2026
A Story Book Christmas at Pickering Museum Village
November 28/29, December 5/6, 2026
Canadian Pacific Holiday Train in Oshawa and Bowmanville
Bowmanville – November 29, 2 – 2:30 p.m.
Oshawa – November 29, 3:15 – 3:45 p.m.
Vaughan – November 30, 10:15 – 10:45 a.m.
Pingle’s Red and Green Christmas Whobilation – TBD
Weekend’s in December
Pingle’s 19+ Ugly Christmas Party – TBD
TBD
Jingle & Roar Christmas Market – TBD
TBD
Bowmanville Christmas Moonlight Magic and Market
Friday, December 4, 2026
Uxbridge Holiday Trail – TBD
TBD
Ajax Spectacle of Lights and Family New Years Eve Party
November 28 & December 31, 2026
Headwaters

Spirit Tree Artesian Craft Market
Saturday November 14, 2026
Merry & Bright Christmas Tour – TBD
TBD
Downey’s Christmas at the Farm
November 28 – December 20, 2026
Farmstead Christmas at Maple Grove Farm and Market – TBD
TBD
Erin Hill Acres Christmas Experience
Various dates, November 14 – December 20, 2026
Museum of Dufferin Holiday Treasures Arts and Crafts Sale
November 25th – December 6th, 2026
Alton Mill Arts Centre Holiday Open House
Saturday, November 21, 2026
Joy + Lights Festival Orangeville
Friday, November 20, 2026
Orangeville Christmas in the Park
Opening Night – Tuesday December. 1, 2026
Runs December 2 – 31, 2026
Erin Window Wonderland
November 20, 2026

Santa Claus Parades
What are the holidays without those beloved local Santa Claus parades? Here are just a few to get you started on planning which parades you’d like to visit this winter:
- Uxbridge: Saturday, November 21, 2026 – https://www.uxbridge.ca/explore-and-play/events/santa-claus-parade
- Newmarket – Saturday, November 21, 2026 – https://www.newmarket.ca/community-and-culture/events-meetings/2026-11-21-santa-claus-parade
- Oshawa Santa Claus Parade of Lights: Saturday, November 21, 2026 – https://www.durhamregion.com/news/santa-claus-parade-returns-to-downtown-oshawa-nov-21/article_abba6fa5-4c1a-5dc1-ae42-b1c7cbd88f34.html
- Orangeville: Saturday, November 21, 2026 – https://www.orangeville.ca/en/things-to-do/orangeville-santa-claus-parade.aspx
- Aurora: Saturday, November 21, 2026 – https://www.aurora.ca/recreation-arts-and-culture/specialevents/santa-under-the-stars-parade/
- Beaverton: Saturday, November 28, 2026 – https://choosebrock.ca/events/event/the-beaverton-santa-claus-parade/
- Erin: Saturday, November 28, 2026 – https://www.erin.ca/living-here/events/events/erin-lions-santa-claus-parade
- Port Perry: Saturday, December 5, 2026, https://business.northdurhamchamber.ca/event-calendar/Details/2026-santa-claus-parade-float-registration-1868596?sourceTypeId=Website
- Schomberg: Saturday, December 5, 2026 – https://www.amainstreetchristmas.com/
- Sunderland: Saturday, December 12, 2026 – https://choosebrock.ca/events/event/sunderland-santa-claus-parade/
To find more fun things to do in YDH, visit our events calendar!
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