Trail Running Calendar near Oakville 2026-2027

August 2026

Urban Trail

A 3 hour urban adventure run in Hamilton for teams of two navigating to scored checkpoints using maps and a smartphone app while remaining on foot and self supported.

September 2026

Sep

12

Sa

Zulu Challenge Mississauga

Mississauga | 14 km from Oakville

Obstacle Run 9 km

A survival-style family obstacle challenge in Mississauga for adults, children and dogs at Paramount Fine Foods Centre on September 12, 2026.

Sep

19

Sa

Kelso Ascension Challenge

Milton | 16 km from Oakville

Trail Run Backyard Ultra 5 km

Timed-loop endurance trail running at Kelso Conservation Area on September 19 2026 with multiple race formats, aid stations and chip timing.

Sep

26

Sa

Brampton Tough Run

Bramalea | 29 km from Oakville

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

Hamilton | 28 km from Oakville

Trail Run 5 km 10 km Half Marathon

Chip-timed urban trail races in Hamilton on September 27, 2026, with 5 km, 10 km, 21 km and kids races through King's Forest and the Bruce Trail.

October 2026

Oct

3

Sa

5 Peaks - Heart Lake

Brampton | 30 km from Oakville

Trail Run 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

Hamilton | 28 km from Oakville

Trail Run 5 km 11 km 27 km 53 km

Looped trail races at Christie Lake on primarily dirt trails, with distances from 5 km to 53 km, cup-less aid stations, and fundraising for Oceana Canada.

Oct

25

Su

Raid the Hammer

Hamilton | 28 km from Oakville

Trail Run 15 km 25 km

Team point-to-point adventure run in Waterdown, Ontario on October 25, 2026 combining road and trail running, navigation and trekking over courses of about 10 to 25 km.

November 2026

Nov

7

Sa

The Beav Trail Race

Milton | 16 km from Oakville

Trail Run 10 km 25 km 50 km

Trail race at Hilton Falls with 10 km, 25 km and 50 km options on groomed and technical trails, planned aid stations, finisher medals and race apparel.

Nov

7

Sa

Oakville Remembrance Trail Run

Oakville

Trail Run 5 km 11 km

An annual Lions Valley trail run on Saturday November 7, 2026 honoring veterans and raising funds for Wounded Warriors Canada, with 5 km and 11 km options.