Trail Running calendar near Roscoe 2025-2026

Quiet Silence in Lake Mills, WI on Dec 5 and 6, 2025 features 50k and 25k out and back runs on the scenic Glacial Drumlin State Trail from Rotary Park. Mostly flat crushed gravel, clocked finishes and awards for top finishers.

Brave winter trails at Governor Dodge State Park with 50K, 25K and 15K courses across rolling single track and prairie. Marked trails, limited aid and a cupless policy mean you must carry your own hydration and winter gear.

Join Strong As Oak and Varsity Rush at Oakhurst Forest Preserve in Aurora on Dec 6, 2025 for 5K and 10K trail races plus kids events on mixed terrain. Hilly course, varied surfaces and finisher medals for all.

Tour de Trails is a winter trail race series around Rockford, Illinois featuring four scenic races from 3 to 12 miles between Dec 20 and Mar 21. Expect snow and ice for a memorable community running challenge that supports Rockford Road Run..

Run winter single track in Crystal Lake at the Frozen Gnome on Jan 10, a Triple Black Diamond loop through Veteran Acres. Choose 50K, 10K or 50K relays for teams of 2 or 5 and warm up at the Gnome Depot with hot food and coffee.

Kick off your trail season in Crystal Lake with the 50K MASHUP SLAM on January 10, 2026. Join a Midwest series of challenging 50K and 53K races that reward cumulative finish times and finisher buckles.

Take on the Whitewalker Ultra 100k in Palmyra WI, a two loop 100k over scenic Ice Age Trail and Scuppernong trails. Expect rugged single track, aid stations on course, and a 24 hour finish limit for a true winter challenge.

The Tour de Trails - Rockford will take place in Rockford on Saturday 17 January 2026. You can run between 3 and 12 miles.

Tackle the Fox Valley Winter Challenge 5K at Dick Young Forest Preserve, the first of a three race trail series that may feature snow, slush or mud. Finishers get a medal and single race entrants receive a cozy winter hat.

Chill out and race the Frozen Tundra IPA 5K along the Des Plaines River Trail in Lincolnshire, then warm up at a lively post race party at Half Day Brewing with beer, food and prizes. Limited to 300 spots so register early.

On February 7, 2026 join the Frozen Assets 5K in Madison and run or skate across the frozen surface of Lake Mendota, starting and finishing at The Edgewater. Enjoy scenic views of downtown and the UW Madison campus during the Frozen Assets..

Run the Fox Valley Winter Challenge Trail Series 8K in Aurora on Feb 21, the middle race on a scenic but wintry trail with woods, open paths and possible snow or mud. All finishers get a medal and single race participants receive a cozy win..

The Tour de Trails - Rockford will take place in Rockford on Saturday 21 February 2026. You can run between 3 and 12 miles.

Run scenic Driftless trails at Governor Dodge State Park on March 7, 2026, choosing from 10K, 27K, or rugged 50K courses. Support local conservation while enjoying stocked aid stations, a custom Silo bag and a horseshoe finisher medal.

Get muddy on wooded single and double track through the historic Lemont Quarries at Muddy Shamrock at The Forge with a half marathon or quarter marathon. Expect rugged terrain, chip timing, awards, a tee and a lively post race party.

Take on the Skunk Ape 806 314 Trail Race at Lowell Park with 33.75 mile and 13.5 mile solo options or a team 806 relay. Alternate wooded loops, enjoy hearty aid station fare and finisher swag, and chase podium awards and great camaraderie.

The Tour de Trails - Rockford will take place in Rockford on Saturday 21 March 2026. You can run between 3 and 12 miles.

Wrap up winter on scenic mixed trails at the Fox Valley Winter Challenge 10K in St. Charles on March 22, 2026. Expect varied footing, a finisher medal and cozy winter hat, plus bundle pricing if you tackled other series races.

Chauncey’s 4 at The Farm is a friendly spring trail run at St James Farm in Winfield, IL, featuring a scenic 4 mile loop over limestone and wooded paths. Join the Dick Pond Trail Race Series and earn a collectible finisher woodallion.

Trailbreaker in Waukesha invites runners to scenic courses along Glacial Drumlin and Fox River trails, with distances from marathon to Kids 1K. New ruck events add variety while proceeds support local parks and the urban forest.