Oakville

Trail Running Calendar near Oakville 2026-2027

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Explore the top trail runs near Oakville for 2026-2027! We've gathered 8 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

October 2026

Sticks N' Stones Trail Race

Hamilton | 28 km from Oakville

Trail Run 5 km 11 km 27 km 53 km

Looped trail race at Christie Lake with 5.3 km laps, multiple distances, cup-less aid stations, and proceeds supporting Oceana Canada.

Looped trail race at Christie Lake with 5.3 km laps, multiple distances, cup-less aid stations, and proceeds supporting Oceana Canada.

Raid the Hammer

Hamilton | 28 km from Oakville

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.

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

The Beav Trail Race

Milton | 16 km from Oakville

Trail Run 10 km 25 km 50 km

Trail races at Hilton Falls on November 7, 2026 offering 10 km, 25 km and 50 km options, sanctioned by Athletics Ontario and supporting MedVents.

Trail races at Hilton Falls on November 7, 2026 offering 10 km, 25 km and 50 km options, sanctioned by Athletics Ontario and supporting MedVents.

Oakville Remembrance Trail Run

Trail Run 5 km 11 km

An annual trail run in Lions Valley offering 11 km and 5 km distances to honour veterans and raise funds for Wounded Warriors Canada.

An annual trail run in Lions Valley offering 11 km and 5 km distances to honour veterans and raise funds for Wounded Warriors Canada.

Golden Leaf Orienteering Fest

Burlington | 18 km from Oakville

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.

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

Sulphur Springs Trail Race

Hamilton | 28 km from Oakville

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

2-4-Go

Burlington | 18 km from Oakville

Trail Run 90 min

Adventure orienteering across Southern Ontario May 16 to 18 2026 with timed Choose Your Adventure formats and virtual MapRun courses.

Adventure orienteering across Southern Ontario May 16 to 18 2026 with timed Choose Your Adventure formats and virtual MapRun courses.

August 2027

Raid the City

Hamilton | 28 km from Oakville

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.

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.