Madison
Trail Running Calendar near Madison 2026-2027
Explore the top trail runs near Madison for 2026-2027! We've gathered 9 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
September 2026
A women only Last Woman Standing trail event on a roughly one to 1.25 mile loop with 250 to 300 ft of climb per lap near Arena Wisconsin. Laps repeat every 20 minutes until one runner remains.
October 2026
Two trail routes around Indian Lake County Park in Cross Plains, Wisconsin feature wetlands, forested slopes, and a section of the Ice Age Trail. The event is cup free and includes post-race music, food, and awards.
A community 2 mile cross country run with a virtual option at Glacier Creek Middle School on October 3, 2026, featuring packet pickup, awards, live timing, and local fundraising.
November 2026
December 2026
Embrace the winter night on a flat rails to trails course in Lake Mills with 17.5 or 31 mile distances and a unique quiet atmosphere.
May 2027
Trail races at Donald County Park offering 5 km, 15 km and a Kids One Mile Fun Run with proceeds supporting Friends of Donald Park for trail maintenance.
Rumble on the Ridge is a backyard ultra style last person standing race near Arena, Wisconsin, run on a 1 to 1.25 mile loop with 20 minute laps. The course reverses direction every four hours and includes 250 to 300 feet of elevation gain per lap.
Out-and-back trail event in Belleville, Wisconsin offering 50 mile, 50K, and Half Marathon distances on the Badger and Sugar River rail trails with regular aid stations.