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Trail Running Calendar near Milton 2026-2027

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Explore the top trail runs near Milton for 2026-2027! We've gathered 15 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

Trail Running Calendar Canada
August 2026
Aug
30
Su

Raid the City

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

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

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

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
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.
Sep
27
Su

Pace for the Donkeys 5K Trail Run

Trail Run 5 km
A charity trail event at the Donkey Sanctuary of Canada in Puslinch offering a 5K trail run and a 1K option with fundraising for the sanctuary.
Sep
27
Su

Traverse the Valley

Trail Run 5 km 10 km
An on trail point to point race in Dundas on September 27, 2026 offering approximate 10 km and 5 km options with map navigation and checkpoints.
October 2026
Oct
3
Sa

5 Peaks - Heart Lake

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

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
24
Sa

The Lost Valley Trail Race

Trail Run 10 km 25 km
Point-to-point trail races on October 24, 2026 along the Bruce Trail between Burlington and Dundas, offering 10 km and 25 km options with bus transfers and aid stations.
Oct
25
Su

Raid the Hammer

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

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

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.
Nov
7
Sa

Murphy's Mission

Trail Run 5 km 10 km
Canicross and human 5 km and 10 km races at Christie Lake supporting Hamilton Animal Services, with timed loops, gear checks, and fundraising for shelter adoptions.
May 2027
May
22
Sa

Sulphur Springs Trail Race

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