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Trail Running Calendar Ontario 2026-2027

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Monthly updates for Ontario

Get new running races (and updates) in your inbox every month.

Explore the best trail runs in Ontario for 2026-2027! Our updated list features 56 exciting races across the region. Find your next race in Ontario below and join the running community at these great events!

January 2026
Jan
17
Sa

Polar Paws Trail Race

Trail Run 5 km 10 km 25 km
February 2026
Feb
1
Su

Kawartha Lakes Winter Festival

Trail Run
March 2026
Mar
28
Sa

DSpring Fling 5km

Trail Run 5 km
April 2026
Apr
11
Sa

Caledon Crusher

Trail Run 25 km 50 km 72 km
Apr
18
Sa

The Foxtail Rail Trail Race

Trail Run 5 km 10 km 25 km 50 km
Apr
25
Sa

Pick Your Poison Trail Run

Trail Run 13 km 25 km 50 km
May 2026
May
2
Sa

The Rugged Raccoon Night Race

Trail Run 10 km 25 km 50 km
May
2
Sa

5 Peaks - Kelso

Trail Run Half Marathon
May
2
Sa

Pure Grit Trail Race

Trail Run 3 km 5 km ... 30 km 6 hr
May
9
Sa

Conquer The Canuck

Trail Run
May
9
Sa

Seaton Scramble Trail Race

Trail Run 7 km 15 km 25 km 50 km
May
15
Fr

The First Hour

Trail Run 8 km
May
23-24
Sa - Su

Sulphur Springs Trail Race

Trail Run 10 km 20 km ... 100 km 100 mi
May
30
Sa

Tails on Trails

Trail Run 3 km 5 km
May
30
Sa

Great Mansfield Outdoors

Trail Run 5 km 10 km ... 50 km 100 km
June 2026
Jun
6
Sa

5 Peaks - Crawford Lake

Trail Run
Jun
7
Su

Hope in Motion - Caledon

Trail Run 5 km 10 km
Jun
10
We

The Ribbon 200

Trail Run 73 km 100 mi 200 mi
Jun
13
Sa

Boomerang Trail Run

Trail Run 2 hr 4 hr 6 hr
Jun
13
Sa

Look Out Trail Race

Trail Run 7 km 14 km Half Marathon