Trail Running calendar near Roscoe 2025-2026

Join the Bucks & Does 13.1 Pointer on November 15, 2025 in Nashotah Park for scenic wood chip trail races including a half, 10K, 5K and a kids Bambi Run. Enjoy shaded paths, chip timing and a unique finisher woodle.

Explore scenic quarry and canal trails at The Forge in Lemont with distances from 10K up to a bold 60K. Expect varied single and double track, a few technical sections, and a lively fall trail festival atmosphere.

Run the 53rd Rockford Road Runners Thanksgiving Turkey Trot on Nov 27 for a rugged 5k trail at Atwood Park with hills, rocks and roots. Enjoy holiday fun while supporting the Rock River Valley Food Pantry and local youth programs.

Run the peaceful Glacial Drumlin State Trail at the Quiet Silence 50k in Lake Mills, WI, with 50k and 25k routes on crushed gravel. This timed race awards top finishers and asks runners to keep quiet for nearby neighborhoods.

Event overview The Guv'nor Frozen 50 takes place on December 6, 2025 at Governor Dodge State Park, Twin Valley Picnic Area, Dodgeville, WI. Distances offered are: 50K 25K 15K Parking requires a park pass; self-service kiosks are available..

Take on the Frozen Gnome, a winter trail race in Crystal Lake offering 50K, 10K and relay teams. Hilly single track, hot aid station fare and medals make for a cozy but challenging day on trails.

Event overview The 50K MASHUP SLAM is a series of trail races in the Midwest based on the 50K distance. The series includes multiple events across the year, begins with the Frozen Gnome 50K in January and concludes in November with the Mine..

Whitewalker Ultra 100k is a self-supported ultramarathon held in Palmyra, Wisconsin, starting at Emma Carlin Trailhead. The course comprises two 50k loops, first looping west on the Ice Age Trail to Whitewater and back, followed by a second..

Take on the Fox Valley Winter Challenge, a three race trail series across Batavia, Aurora, and St Charles this winter. Choose a 5K, 8K or 10K or grab the full series and earn gear from a hat to a sweatshirt as you run scenic forest preserve..

The Frozen Assets 5K Run/Walk is a unique winter event held in Madison, Wisconsin, where participants run or walk entirely on the frozen surface of Lake Mendota. The 5K course offers scenic views of downtown Madison and the University of Wi..

ARKTOS : February 28 to March 1, 2026 ARKTOS is a winter trail ultra held in Dousman, Wisconsin (Southern Kettle Moraine Forest). The event offers timed-loop formats in three durations. The race is open to solo runners and relay teams of up..

Muddy Shamrock @ The Forge is a trail running event held at The Forge: Lemont Quarries in Lemont, Illinois. The race offers two distances: Trail Half Marathon (about 13.1 miles, run as two laps) and Trail Quarter Marathon (about 6.6 miles,..

Skunk Ape 806/314 Trail Race : March 21, 2026, Dixon, IL The event takes place at Lowell Park, 2114 Lowell Park Road, Dixon, IL 61021 on March 21, 2026. Distances offered: 806 - 33.75 miles (8 hrs 6 mins) 314 - 13.5 miles (3 hrs 14 mins) 8..

Trailbreaker : March 29, 2026, Waukesha, WI The Trailbreaker is scheduled for March 29, 2026, in Waukesha, WI, with the main venue at the Schuetze Recreation Center / Frame Park Baseball Stadium. The event has been hosted by the Park Founda..

Celebrate Earth Day on April 18 in Crystal Lake with looped trail races of 50K, 15 mile, and 5 mile on rolling single track. Friendly aid station, scenic pond start, and relaxed festival vibe for trail runners of all levels.

Childish Nonsense brings looped ultrarunning to Deer Grove Forest Preserve in Palatine IL with races from 10K to 50 mile. Expect mellow trails, multiple laps with a main aid station about every 5.5 miles, and a welcoming, inclusive communit..

The Prickly Pine Jackpot 24 Hour Solo/Relay is an endurance running event held in the scenic Kettle Moraine State Forest near Dousman, Wisconsin. Participants can choose from multiple race options including 6-hour, 12-hour, and 24-hour solo..

The Donald Dash Trail Run is a popular trail running event held at Donald County Park in Mount Horeb, Wisconsin. It offers two race distances: a 5K for beginners and a more challenging 15K for experienced runners. The course features divers..

Run the F^3 Cap Sauers Trail Marathon or 10 Mile at Teason's Woods in Palos Hills on May 9, 2026, and enjoy scenic wide horse trails with gentle rolling terrain. All finishers get a wooden medal and event apparel, plus post race chili and b..

Push your limits at the Chicago Yeti 7 to 11 hour Endurance Run in Willow Springs, a looped trail through restored forest and rolling hills with pond views. Live lap timing and a playful aid station keep you on pace and fueled.