Trail Races in Oakville
Upcoming1raceNext upOct 25, 2026ThroughOct 2026
Browse 1 upcoming trail races in Oakville, with dates, venues, distances, and registration details for each listing. From neighborhood fun runs to established city events, find your next trail start line in Oakville.
Upcoming Featured Races in Oakville
Trail Races in Oakville 2026
Spotlight races
August 2026
September 2026
Trail
2026 5 Peaks Trail Running Series: Albion Hills
Sep 5, 2026
Caledon, ON
Trail
2026 Island Lake Classic
Sep 7, 2026
Orangeville, ON
10K0.2K5K
Trail
2026 Summer Shores 5K/8K
Sep 7, 2026
Hamilton, ON
8K1K5K
Trail
UNFINISHED Series 2026
Sep 12, 2026
Toronto, ON
6.71KUltra15 Hour
Trail
2026 Beat Bechtel
Sep 13, 2026
Waterloo, ON
5K
Trail
2026 Don Doan Dash
Sep 13, 2026
Brampton, ON
5K10K
Trail
2026 Monarch Ultra 10km
Sep 19, 2026
Peterborough, ON
10K1K
Trail
Harvest Trailmixer Fundraiser for Mental Health 2026
Sep 19, 2026
Guelph, ON
2.5K5K10K1K
Trail
Kitchener Kids with Cancer 2026
Sep 19, 2026
Kitchener, ON
Trail
2026 Trail Party: Walk, Hike, or Run for rare
Sep 20, 2026
Cambridge, ON
Walk5K
Trail
2026 BLUE BULLY ULTRA
Sep 25, 2026
The Blue Mountains, ON
50K25K5K
Trail
Strom's Harvest Hustle 2026
Sep 26, 2026
Guelph, ON
5K
Trail
2026 PACE FOR THE DONKEYS 5k TRAIL RUN
Sep 27, 2026
Wellington County, ON
5K1K
Trail
2026 Run for the Grapes Half Marathon & 5K
Sep 27, 2026
Lincoln, ON
5KHalf Marathon
Trail
Albion Ascent Trail Race 2026
Sep 27, 2026
Hamilton, ON
1K3K5K10K+1
October 2026
Trail
2026 5 Peaks Trail Running Series: Heart Lake
Oct 3, 2026
Brampton, ON
Trail
Rally in the Ravine 2026
Oct 3, 2026
Toronto, ON
10K5K1K
Trail
West Rouge Sports & Recreation Association Fun Run 2026
Oct 3, 2026
Toronto, ON
10K5K
Trail
2026 Collingwood 10k
Oct 4, 2026
Collingwood, ON
5K10K1K
Trail
Run The Caves 2026
Oct 4, 2026
Warsaw, ON
Ultra1K50K25K+2
Showing 24 of 40 races