Trail Running calendar near Caledon 2026-2027

Join the Dion Mighty Chickadee Snowshoe Race at Cold Creek for a scenic 6.5 km through forest and meadow with a few climbs. Limited entries, snowshoe rentals and post run food plus awards make this a fun winter challenge.

Run the DSpring Fling 5 km along Hamilton's scenic waterfront and Bayfront Park on a flat, traffic free, fan friendly course. Enjoy chip timing, a custom finisher medal and post race food and photos.

Tackle the rugged Caledon Crusher on the Bruce Trail with 25k, 50k or epic 72k options featuring technical singletrack and big climbs as you finish at Mono Centre Park in Shelburne. Support the Bruce Trail and refuel at well stocked aid sta..

Challenge yourself on the Foxtail Rail Trail Race in Dundas Valley, offering 5, 10, 25 and 50 km options on a fast, wide rail trail with start and finish at the Trail Centre. Enjoy aid stations, chip timing, race photos and finisher medals..

Take on scenic, hilly single loop trails at Pick Your Poison Trail Race in Copeland Forest with 12.5k, 25k or 50k options, three aid stations per loop and challenging elevation. This nonprofit event benefits local mental health programs and..

Join the 5 Peaks Trail Running Series at Kelso in Milton for forest trails with steep climbs and flowing descents. Pick distances from kids races to 20.6 km and enjoy scenic singletrack, aid stations and a lively finish.

Explore the Seaton Scramble Trail Race in Pickering on May 9, 2026 with scenic single and double track, creek crossings, stairs and viewpoints. Distances from a kids 1K to a challenging 50K suit every trail runner.

Sulphur Springs Trail Race in Dundas Valley, Hamilton on May 23 and 24 offers looped 20K terrain with distances from 10K to 100 miles plus team relays. Rugged trails, big climbs, and crew access make for a classic spring ultra.

Join Tails on Trails on May 30, 2026 at Bechtel Park in Waterloo to support Humane Society of Kitchener Waterloo and Stratford Perth. Choose 2.5 km or 5 km loops, bring your pup or run solo, and help raise funds in a fun family atmosphere.

Great Mansfield Outdoors on May 30, 2026 showcases rooty single track through Mansfield Outdoor Centre and Dufferin County Forest, with distances from 5K to the new 100K solo or 100K relay. Expect big climbs, camping and on course aid.

Join Hope in Motion 2026 on June 7 in Caledon East for a community fundraiser supporting CMHA Peel Dufferin with cycling, walking, running and rolling for all abilities. Choose distances from 5 km trails to 100 km rides and help raise funds..

Experience rugged singletrack, sweeping views and big climbs along the Bruce Trail at the Ribbon 200, June 10 to 14, 2026, with 200 mile, 100 mile and 72.5 km E2E options around the Blue Mountains. Fully supported with stocked aid stations..

Run Uxbridge offers scenic trail and road 10K, 5K and 1 km kids dash starting and finishing at Elgin Park in Uxbridge, Ontario. Enjoy a community race with age category awards and support for the Uxbridge Hospital Auxiliary.

Tackle technical singletrack and big climbs in Durham Forest at The Whole Enchilada on June 20, 2026, with distances from a 1 km kids dash to a challenging 50 km. Eco friendly cup free event at Trail Hub with aid stations and onsite awards.

Join the Sunburn Solstice Trail Run at Marydale Park for a scenic, time based trail challenge with solo and team relay options on tree covered loops. Enjoy community vibes, gear demos and help send kids with disabilities to camp.

Run scenic Bruce Trail singletrack and Kelso Conservation Area on 10 km, 25 km or 50 km courses at the First Blaze Trail Race 2026. Fields capped at 200, with a finisher medal, shirt option, shuttle and a charity donation.

ENDURrun Prelim is a six stage 60 km running challenge across southern Ontario from July 13 to 18 2026. Enjoy road, trail, cross country and track stages around Waterloo and Cambridge for a varied and fast paced multi terrain adventure.

The 5 Peaks - Area 8 will take place in Milton on Saturday 18 July 2026. You can run between 8 and 24 kilometers.

Tally in the Valley Trail Race brings runners to Dundas Valley for scenic 7 km loops through Carolinian forest and rolling hills. Distances range from 7 km to a 100 mile challenge with a custom buckle for 100 milers while supporting SickKid..

Take on the rugged Bruce Trail from Beaver Valley Ski Club in Eugenia Ontario with a challenging trail marathon, half marathon, or both. Expect rocky, very hilly terrain, small fields, gear demos, and proceeds to the local Bruce Trail club.