Milton
Trail Running Calendar near Milton 2026-2027
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.
October 2026
November 2026
Two days of orienteering in the Waterdown area on November 21 and 22, 2026 with a Classic at Mount Nemo, a Sprint at Joe Sams Park and an Ontario Cup at Rockcliffe Trails.
May 2027
Trail running at Kelso Conservation Area with distances from 1 km to 20.6 km, on course aid stations, and awards for top finishers.
Adventure orienteering across Southern Ontario May 16 to 18 2026 with timed Choose Your Adventure formats and virtual MapRun courses.
June 2027
July 2027
A multisport day at Kelso Conservation Area near Milton featuring Swimrun (10K and 20K), open-water swims (1K, 3K, 5K) and 7.5K and 15K trail runs.
Trail running at Area 8 Conservation Area in Milton with multiple race categories including Kids 1K and 3K, former quarry trails, cup free event and on site parking.
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 with 21k, 10k, 5k and kids races across paved paths, dirt trails and technical Bruce Trail sections; aid stations and an included toque.
October 2027
Trail event at Heart Lake Conservation Park on October 2, 2027 offering Grit, Enduro, Sport and a Kids 3K, with water stations and limited parking.