Headwaters
Trails and Ales Event at Mansfield
Saturday January 17 & February 14, 2026
Fire and Ice Festival
January 31 & February 1, 2026
Ignite the Night
Saturday nights in January – March
Island Lake Conservation Area Ice Fishing Derby
February 10 – 19, 2026
Polar Rush Winter Obstacle Course
Saturday, February 28 2026
Theatre Orangeville: Murder at Ackerton Manor
March 12 – 29, 2026
York Region
Jazzlicious Winterfest
January 14 – January 17 & February 4 – February 7, 2026
Wintersong Music Festival
January 22 – 24 2026
Sunday Sip & Create at McMichael Canadian Art Collection
January 25 and February 22, 2026
Grand Shanghai Circus
Saturday, January 31, 2026
Newmarket Main Street Ice Lounge
TBD
SnoFest at The ROC
Saturday, February 7, 2026
Richmond Hill Winter Carnival
February 7 & 8, 2026
Beauty & The Beast performed by Dufflebag Theatre
Family Day, Monday, February 16, 2026
Taste of Georgina
February 16 – March 15, 2026
Unionville Theatre Company: Matilda The Musical
February 19 – 22, 2026
LunarFest at the Varley Art Gallery
February 21 – 22, 2026
Durham
Lake Simcoe Ice Fishing Derbies
January 1 – March 15, 2026
Book Drunkard Festival
Various dates January 18 – May 3, 2026
Ontario Philharmonic Shows
January 24 & March 20, 2026
Oshawa Generals Game
Throughout Winter 2026
Candlelight Concert
Various dates in January & February
Scugog Pond Hockey Tournament
Saturday, February 7, 2026
Classic Movie Night
First Thursday of each month
Family Day Choose Your Adventure at The Glen
Monday, February 16, 2026
Ajax Winterfest
Monday, February 16, 2026
For more events in YDH, visit our events calendar!
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