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Trail Running Calendar near Waterloo 2026-2027

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Explore the top trail runs near Waterloo for 2026-2027! We've gathered 11 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.

August 2026
Aug
9
Su

The ENDURrun

Trail Run 10 km 15 km ... Marathon 160 km
Eight stage 80 km multi discipline running event in Ontario combining road, time trial, cross country, trail and track from August 9 to 16, 2026.
September 2026
Sep
13
Su

Beat Bechtel

Trail Run 5 km
Trail 5 km at Bechtel Park on September 13, 2026, chip timed with reusable chips and minimal extras, free for Run Waterloo members.
Sep
19
Sa

Kitchener Kids with Cancer

Trail Run Walk 5 km 10 km
Fundraising run at Kiwanis Park supporting the Pediatric Oncology Group of Ontario with timed 5 km and 10 km races, a kids 200 m event, shirts and finisher medals.
Sep
20
Su

Rare Trail Party

Trail Run Walk 5 km
Fundraising trail event in Cambridge offering a walk, a hike or a 5K run along the Grand Trunk Trail with education stations, music and a BBQ at the ECO Centre.
Sep
26
Sa

Strom's 5K Harvest Hustle

Trail Run Walk 5 km
A recreational 5K trail run and walk on September 26, 2026 at Strom’s Farm and Bakery in Guelph featuring a cedar spiral, corn maze sections, dirt paths and post run treats.
Sep
27
Su

Willibald Pasture Dash

Trail Run 5 km 10 km
A pasture cross country race at Willibald Farm in Ayr with 5 km and 10 km options and proceeds supporting rare Charitable Research Reserve.
October 2026
Oct
4
Su

The Hustle at Pinehurst

Trail Run 13 km 25 km 50 km
Trail event on October 4, 2026 at Pinehurst Lake with a 12.5K loop and 25K, 50K and 50K relay options. Mostly natural singletrack around forest, lake and meadows with aid stations and a cup free policy.
Oct
17
Sa

Wise Raven Trail Race

Trail Run 5 km 10 km 25 km 50 km
Looped trail race at Camp Heidelberg in Waterloo offering 5 km to 50 km options, sanctioned by Athletics Ontario and timed by Chiptime Results.
Oct
31
Sa

Trick or Trot - Waterloo

Trail Run 5 km
Halloween themed running event in Waterloo Ontario with a 5K, a 200 m fun run, a pre race costume contest, and medals for all participants.
January 2027
Jan
30
Sa

Polar Bear Run - Fergus

Race Roster Trail Run Walk 5 km 10 km Half Marathon
Winter trail runs in Fergus and Elora with 5k, 10k and Half Marathon options, chip timing, medals and fundraising for Servant's Heart.
Polar Bear Run - Fergus
July 2027
Jul
10
Sa

The 5K Foam Fest - Kitchener, ON

Race Roster Obstacle Run Walk 5 km
An obstacle course 5K at Victoria Park on July 10, 2027 featuring over 25 optional obstacles, a kids zone, food vendors and a beer garden.
The 5K Foam Fest - Kitchener, ON
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