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Trail Running Calendar near Oakville 2026-2027

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Explore the top trail runs near Oakville for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
30
Su

Raid the City

Urban Trail
Raid the City is a three hour urban adventure run for teams of two in Hamilton. Teams use maps and a smartphone app to score checkpoints across trails, roads, alleys and parks while travelling on foot.
September 2026
Sep
12
Sa

Zulu Challenge Mississauga

Obstacle Run 9 km
A family oriented obstacle challenge in Mississauga with courses for adults, children and dogs at the Paramount Fine Foods Centre.
Sep
27
Su

Albion Ascent Trail Race

Trail Run 3 km 5 km 10 km Half Marathon
A chip-timed, transit-friendly trail race in King’s Forest, Hamilton on September 27, 2026, offering distances from kids runs to a 21 km Bruce Trail course, aid stations and a Canadian made toque.
October 2026
Oct
3
Sa

5 Peaks - Heart Lake

Trail Run Walk 3 km 8 km 15 km 23 km
Trail races at Heart Lake Conservation Park around a spring-fed kettle lake, with distances from 3 km to 22.5 km and aid stations on course.
Oct
10
Sa

Sticks N' Stones Trail Race

Trail Run 5 km 11 km 27 km 53 km
Trail race at Christie Lake Conservation Area on a 5.3 km loop with distances from 5 km to 53 km and aid stations on every loop.
Oct
25
Su

Raid the Hammer

Trail Run 15 km 25 km
Team-based adventure run in Waterdown combining road, trail, navigation and trekking with Raid (20–25 km) and Half-Raid (10–15 km) options.
November 2026
Nov
7
Sa

The Beav Trail Race

Trail Run 10 km 25 km 50 km
Trail races of 10 km, 25 km and 50 km at Hilton Falls on November 7, 2026 with technical sections, aid stations and a 9 hour cutoff for the 50 km.
Nov
7
Sa

Oakville Remembrance Trail Run

Trail Run Walk 5 km 11 km
A November 7, 2026 trail event in Lions Valley offering 11 km and 5 km routes to honour veterans and support Wounded Warriors Canada. Registration opens spring 2026.
May 2027
May
22
Sa

Sulphur Springs Trail Race

Trail Run 10 km 20 km ... 100 km 161 km
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