Trail Running calendar near Freeport 2026-2027

Last Dot Standing in Belleville WI alternates repeated 4.2 mile legs between Belleville Community Park and Dot's Tavern until one runner remains. Separate 24 hour and 48 hour races use the same course and offer distance buckles and prize pa..

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

A non-timed 2K and 5K trail run/walk at Case Creek Valley that welcomes leashed dogs and supports Rock Island County Animal Care & Control Shelter, with race bibs, optional T-shirts, finisher dog tags, and hydration stations.

Echo 136 in Whitewater, WI is a 136 mile trail ultramarathon on the Ice Age State Trail with a 55 hour cutoff and 10 aid stations. The event lists about 11,148 ft of ascent and is organized by TYDISH Running.

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.

A grassroots looped ultramarathon in Dixon, IL with a roughly 7.85 mile loop and distances to 100 miles. The course mixes singletrack, meadow and gravel, features two aid stations, allows crew and pacers, and awards finishers.

A multi-distance run and walk at Moraine Hills State Park on September 26, 2026 offering 5K, 10K and half marathon options plus a virtual period in September to support Friends of Moraine Hills State Park.

Emmy's Rustic Run is a Fort Atkinson trail run and family fun day raising funds for the A-T Children's Project, featuring a 5k, a one mile walk, kids races and virtual participation.

Trail races at Swiss Valley Nature Center in Peosta, Iowa offer 5.2 mile loops in three distance options, with multiple loops forming the 25K and 50K. Camping, showers, and shuttle service are available for participants.

Point-to-point, all-trail ultramarathon along the Hennepin Canal between Sterling and Colona, Illinois, offering 100 mile, 50 mile, 50K and team relay options with regular aid stations and finisher awards.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.

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-c..

A coffee-themed, untimed fun run at Case Creek Trails on October 4, 2026, offering 2K and 5K routes, hot drinks and aid stations. The event raises funds for the local animal shelter and includes optional swag and finish tokens.

Timed ultraruns in Southern Kettle Moraine Forest on Oct 10 to Oct 11, 2026. Solo runners or teams of up to four complete as many 3, 5, or 6 mile McMiller Trail loops as possible in 6, 12 or 20 hour formats.

Trail ultra at Bethel Horizons in the Driftless Area offering 50K, 20M and 10M looped courses with mixed singletrack, grassy ridgelines, rocky climbs, fully stocked aid stations and chip timing.

Trail 100 mile and 100K races in Dubuque, Iowa on a multi-loop marked course through the Mines of Spain Recreation Area, featuring varied terrain, river views, and substantial loop-based elevation. Organized by Sun Trail Running.

Trail run at Saw Wee Kee Park on October 17, 2026, over soft, twisting trails with variable footing. Bib-timed waves, part of a four-race series with collectible medal pieces and seasonal swag.

Nature-based out-and-back event in Roscoe, IL offering a 5K run or 2 mile walk on mixed gravel and crushed limestone, starting at Roscoe Middle School and passing a water station twice.