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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 12 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

September 2026
Sep
19
Sa

Kelso Ascension Challenge

Trail Run Backyard Ultra 5 km
Timed-loop trail event at Kelso Conservation Area on September 19, 2026, with options from a 1 hour 2 km loop to 6 hour relays and a children's race.
Sep
26
Sa

Brampton Tough Run

Obstacle Run 5 km
A 10th anniversary 5 km bootcamp-style obstacle run at Chinguacousy Park with supervised stations, a free Fan Zone for kids and citywide try-it demonstrations.
Sep
27
Su

Albion Ascent Trail Race

Trail Run 5 km 10 km Half Marathon
Transit friendly, chip timed trail races in Hamilton from kids distances to a 21 km full ascent through King's Forest and the Bruce Trail on September 27 2026.
October 2026
Oct
3
Sa

5 Peaks - Heart Lake

Trail Run 3 km 8 km 15 km 23 km
Trail running at Heart Lake Conservation Park with distances from 3 km to 22.5 km, maps, aid stations, a cup free policy and onsite facilities.
Oct
10
Sa

Sticks N' Stones Trail Race

Trail Run 5 km 11 km 27 km 53 km
Looped trail race at Christie Lake using a 5.3 km circuit for multiple distances, cup-less aid stations, and fundraising support for Oceana Canada.
Oct
25
Su

Raid the Hammer

Trail Run 15 km 25 km
Raid the Hammer is a point to point adventure run in Waterdown featuring trail running and navigation for teams of two or three.
November 2026
Nov
7
Sa

The Beav Trail Race

Trail Run 10 km 25 km 50 km
Trail races at Hilton Falls Ontario offering 10 km, 25 km loop and 50 km two loop option with aid stations, apparel and finisher medals.
Nov
7
Sa

Oakville Remembrance Trail Run

Trail Run 5 km 11 km
Second annual Oakville Remembrance Trail Run on November 7, 2026 offers 5 km and 11 km routes in Lions Valley to support Wounded Warriors Canada.
Nov
21-22
Sa - Su

Golden Leaf Orienteering Fest

Trail Run Urban Trail
A two day orienteering weekend in the Golden Horseshoe on November 21 22 2026 with Classic, Sprint and Ontario Cup mass start races plus a Saturday social.
May 2027
May
22
Sa

Sulphur Springs Trail Race

Trail Run 10 km 20 km ... 100 km 161 km
May
22-24
Sa - Mo

2-4-Go

Trail Run 90 min
Adventure orienteering across Southern Ontario May 16 to 18 2026 with timed Choose Your Adventure formats and virtual MapRun courses.
August 2027
Aug
29
Su

Raid the City

Urban Trail
Raid the City is a three hour urban adventure race for teams of two featuring map navigation and checkpoint scoring across the streets and trails of Hamilton.
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