Trail Running calendar near Freeport 2026-2027

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 ultra in Dixon, Illinois featuring multiple distances on mixed singletrack and meadow paths. The event provides two aid locations, crew and pacer access, and medals or a buckle for finishers depending on distance.

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 Preserve near Peosta, Iowa, offering 5.2 mile, 25k and 50k options on a multi loop course with creek crossings and rugged, hilly terrain. Free camping, showers and shuttle service are provided.

A point to point all trail ultramarathon along the Hennepin Canal State Trail in northwest Illinois, offering 100 mile, 50 mile, team relay and a nighttime 50k, with aid stations every 3 to 7 miles and Western States qualification.

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.

Trail Run at Indian Lake takes place on Oct 3, 2026 at Indian Lake County Park. The event is cup free, includes a free kids run with no registration, and features a post race party with live music and a raffle.

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.

A Midwest trail ultramarathon in Dubuque that uses a roughly 20 mile loop through the Mines of Spain Recreation Area. Options include a 100 mile five loop race and a 100K three loop race with substantial elevation gain.

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.

A memorial 5K run and 2 mile walk in Roscoe, Illinois on October 17, 2026. The out and back course uses local trails and crushed limestone, includes a water station, and offers a virtual supporter option.

Soul Crusher is a trail race in Crystal Lake, IL offering 10 mile and 5 mile options on single track forest trails with looped sections and occasional extra mileage. Packet pickup is available the day before and a 3 hour 30 minute cutoff ap..

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.

A Halloween-themed trail event in Pingree Grove, IL on October 23, 2026 with multiple 5 km heats, haunted sets and animatronics, plus a costume contest, bonfire and food; spectator fee $10, free parking.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.

Miner 49er in Dubuque, IA features 25K and 50K runs on single-track and prairie trails with significant elevation gain, three aid stations, and views of the Julien Dubuque Monument, Horseshoe Bluff, and the Mississippi River.

A trail running event at Camp Big Timber in Elgin, IL on November 8, 2026 offering 3 mile and 5 mile courses plus a Kids Fun Run. The course includes grass, gravel and a creek crossing and supports local youth organizations.

Explore the forest trails and hills of Lake Geneva at this multi distance trail event. Choose from several individual races or join a team relay for a day of outdoor activity and festival atmosphere.