Milton
Trail Running Calendar near Milton 2026-2027
Explore the top trail runs near Milton 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.
November 2026
Two-day orienteering weekend in the Waterdown area on November 21 and 22, 2026 with the Ontario Cup mass start, a sprint at Joe Sams Park and a classic at Mount Nemo.
May 2027
Trail races at Kelso Conservation Area in the 2024 Ontario series, with distances from 1 km kids races to a 20.6 km Grit course.
Adventure orienteering across Southern Ontario May 16 to 18 2026 with timed Choose Your Adventure formats and virtual MapRun courses.
Trail race weekend in Dundas Valley on May 29 and 30 2027 featuring a 20K loop course, multiple distances and team relay options.
June 2027
July 2027
A multisport day at Kelso Conservation Area on July 4, 2027 featuring swimrun races, open water swims and 7.5 km and 15 km trail runs.
August 2027
A three-hour, map-based urban adventure run in Hamilton for teams of two with smartphone app tracking and checkpoints across trails, roads and parks.
September 2027
Trail race in Hamilton offering 21k, 10k, 5k and kids runs through King’s Forest and the Bruce Trail with aid stations and a Canadian-made toque for entrants.
October 2027