Middleton
Trail Running Calendar near Middleton 2026-2027
Explore the top trail runs near Middleton for 2026-2027! We've gathered 14 exciting trail runs in the area. Check out our detailed list below to find your next local trail run.
August 2026
A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.
Trail races at New Glarus Woods State Park on August 15, 2026 include 16K, 8K, 5K and a free 1K kids run. Proceeds benefit Friends of New Glarus Woods State Park and awards include age-group prizes plus a 16K consistency award.
Multi-hour looped trail challenges at Blackhawk Ski Club in Middleton, WI, with individual and team relay options, plus a 1.7 mile fun run that highlights the course features and terrain.
September 2026
A multi day event in Belleville WI with a Last Dot Standing format between Belleville Community Park and Dot's Tavern plus 24 and 48 hour races and long distance buckles.
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/walk at Glacier Creek Middle School with in-person and virtual options, evening and race-day packet pickup, live electronic results, and awards; proceeds support course upkeep and the high school cross-country pro..
An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.
May 2027
Trail races at Donald County Park include 5 km, 15 km and a Kids One Mile Fun Run across prairie, single-track, sand and bridges. Proceeds support Friends of Donald Park for trail maintenance and repair.
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.
An out-and-back trail event in Belleville WI offering a 50 Miler, 50K and half marathon on the Badger State and Sugar River trails.