Trail Running calendar near Freeport 2025-2026

The Chupacabra Trail Races take place in Dixon, Illinois, featuring night trail running on a 5-mile loop course composed of grass, gravel, dirt, and 30% single track. Participants can choose from distances of 5, 10, or 15 miles by completing one to three laps, or join a three-person relay team. The..

The Mines of Spain Trail Races, held in Dubuque, Iowa, offer runners three challenging distances: a half marathon, 7-mile, and 4-mile race. Set in the scenic Mines of Spain State Recreation Area, the courses feature diverse terrain including dirt single and double tracks, prairie grass trails, rocky..

The New Glarus Woods Trail Run is an annual event held at New Glarus Woods State Park in Wisconsin, part of the Savanna Trail Run Series. The 6th edition features multiple race distances: a 1-mile kids fun run, 5 km, 8 km, and 16 km trail runs. The event supports fundraising for mountain bike trail..

Run the Rails is a community running event held in Elburn, Illinois, featuring a 4-mile run, a 7-mile run, and a 1-mile fun run. Presented by the Elburn Parks Commission, the race offers a vibrant atmosphere with opportunities for local businesses to sponsor and gain visibility through banners, race..

The Sun Prairie Community 5k is an annual running event held at Sheehan Park in Sun Prairie, Wisconsin. It features a 5K cross-country race that follows the Sun Prairie High School Cross Country Course, providing participants with an authentic cross-country running experience. In addition to the mai..

Run The Hawk Trail Run takes place at the historic Blackhawk Ski Club in Middleton, Wisconsin. This endurance event offers 3, 6, and 12-hour solo and relay challenges on a scenic 2.25-mile loop course featuring 345 feet of elevation gain per lap. Runners experience diverse terrain including grass pa..

ScoCo50 is a trail running event held at Scott County Park in Long Grove, Iowa, offering 50K, 10-mile, and 5-mile race distances. The course features a mostly dirt and grass trail system through wooded and prairie areas, with gentle elevation gains—approximately 950 feet per 10-mile loop for the 50K..

The Summer Trail Classic is a trail running event held at Paul Douglas Forest Preserve in Hoffman Estates, Illinois. It offers three race distances: approximately 4 miles, 9.5 miles, and 13 miles, providing a true trail running experience on twisting single-track trails. The event is part of the 202..

The Gristmill Grind 10K is a challenging trail race held annually at Franklin Creek State Park in Franklin Grove, Illinois. Known as one of the most difficult 10Ks in the area, the course features technical trails with approximately 800 feet of elevation gain, multiple hill climbs, and four creek cr..

The Hobo Trail Runs, hosted by Rockford Road Runners, take place at Rock Cut State Park in Rockford, Illinois. This annual event offers multiple trail running distances including 10k, 25k, and 50k races, with options to participate in single races or the challenging Triple Crown series (85k total) o..

Dirt Circus - Chicago is a free community running event held in Crystal Lake, Illinois, celebrating local trail running culture. Organized by UltraSignup, the event features a festive atmosphere with a social run, food, raffle prizes, and an expo showcasing local races, run clubs, brands, and busine..

Last Dot Standing is a unique endurance running event held at Belleville Community Park in Belleville, Wisconsin. Participants alternate running 4.2-mile legs between Belleville and Dot's Tavern, a historic local tavern, with one hour to complete each segment. The race continues hourly until only on..

The Tiger 10 Miler is an annual trail race held at Byron Forest Preserve and the Nardi Equine Prairie in Byron, Illinois. The 8th edition of this event features a challenging 10-mile course with twists, turns, and hills through scenic natural areas. Participants receive a custom finisher's medal and..

Hindsight Ultra Trail Runs, held in Dixon, Illinois, offers a grassroots ultra running experience with distances of 25K, 50K, 100K, and 100 miles. The course features a 7.85-mile loop combining roughly 50% singletrack, 30% grassy meadows, and 20% gravel paths, with about 6,200 feet of elevation gain..

The Swiss Valley Trail Races, held in Peosta, Iowa, offer runners three distance options: 5.2 miles, 25K, and 50K. Set within the scenic Swiss Valley Nature Preserve, the course features rugged terrain, creek crossings, and steep inclines, with each 5.2-mile loop climbing approximately 875 feet. The..

The Trail Run at Indian Lake is a scenic trail running event held at Indian Lake County Park in Cross Plains, Wisconsin. The race offers two distances: a long course of approximately 10.5 km and a short course of about 5.8 km. The course begins in a restored sedge meadow near the kettle lake formed..

The Hennepin Hundred is a premier ultramarathon held in Sterling, Illinois, featuring 100-mile, 50-mile, 50K, and 100-mile team relay races. The point-to-point course follows the scenic, flat, and fast Hennepin Canal State Trail, Illinois’ longest multi-use trail, stretching from the Rock River to t..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

The Haunted Heritage Trail Fun Run / Hero Walk in Dyersville, Iowa, offers a festive and spooky running experience with multiple events including a 5K Haunted Heritage Trail Fun Run, a 10K Trail Run, and a 1 Mile Hero Walk. Participants are encouraged to wear Halloween costumes as they navigate a 3...

The Autumn Leaf Run is a 5K trail race held at Oakdale Nature Preserve in Freeport, Illinois. Open to all ages and skill levels, the event offers a scenic course featuring diverse terrain such as wide tree-lined trails, moderate hills, prairie areas, bridge crossings, and single-track trail sections..