Trail Running calendar near Freeport 2026-2027

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.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

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.

Trail endurance runs in the Mines of Spain near Dubuque offering 25K and 50K courses on single track with scenic river and bluff views and three stocked aid stations.

Embrace an autumn adventure at the Big Timber XC Challenge, a trail run featuring a famous creek crossing through the woods of Camp Big Timber. Choose between a 3-mile or 5-mile course on grass and gravel paths. All runners get a shirt and..

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.

Celebrate Thanksgiving with a 2 mile run through the wooded trails of Sheffield Illinois. Wear your best holiday costume for a chance to win prizes at this untimed community event.

A community Turkey Trot through Atwood Park near 5k with chipped timing, common trail obstacles and door prizes. No GPS or timing devices are allowed and donations are collected for local causes.

A winter trail event at Governor Dodge State Park on Dec 5, 2026 offering 50K, 25K and 15K over horse trails, single and double track with multiple aid stations, cup-less hydration, and specific pacer and crewing rules for the 50K.

A four race winter trail series in Dixon, Illinois totaling 31 miles across four dates from December 2025 to March 2026. Distances range from 5K to 20K with series awards and age-category prizes.

A dog friendly trail running event at Lake Geneva Ziplines and Adventures with a 4 mile loop, an 8 mile option, and a focus on Canicross. Awards are reserved for teams running with dogs and all finishers receive a small gift.

A night running event near Lake Mills, WI on a flat crushed‑limestone rails-to-trails course offering 16 and 31 mile out-and-back distances with required lights, reflective gear, and cupless aid stations.

A winter obstacle event in Lake Geneva on January 30, 2027 offering distances from a kids course to a 20K Yeti Challenge, plus a competitive Elite division with cash prizes, team entries, and a virtual race option.

A winter trail ultrarun in Dousman, Wisconsin on Feb 27-28, 2027 offering 6, 12 and 24 hour solo or relay options, winter trail terrain, warming shelters, hot drinks and a post-race meal.

Skunk Ape 806/314 is a looped trail event at Lowell Park in Dixon, IL offering 33.75 mile, 13.5 mile and relay options with time limits, an aid station with food, awards, and nonrefundable registration.