Trail Running calendar near St. Charles 2025-2026

Run through snow and ice this winter in the Tour de Trails, a four race series around Rockford and Byron from Dec 20 to Mar 21. Choose 3, 6, 9 or 12 mile courses and support the Rockford Road Runners.

Warm up your winter running at the Frozen Feet 5k Trail Run on January 3 at Creek Ridge County Park. Enjoy two chilly looped trails with a few hills, grab a free winter hat and gloves, and refuel with snacks and drinks after the finish.

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.

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

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.

Tackle the Yeti Trail Half at Bluhm County Park, a four loop single track course with switchbacks and roots that rewards grit and steady pace. Enjoy a limited edition long sleeve shirt plus a winter hat and gloves while supplies last.

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..

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

Hit the wooded trails at Sunset Hill County Park for the Foot Pursuit 5K, a scenic 3.1 mile run or walk across rolling hills. Enjoy friendly competition, age group awards, and postrace camaraderie in Valparaiso.

Tombstone at Sunset Hill Farm County Park on March 14, 2026 offers 30k, 50k and a new 50 mile on a hillier course with a Roller Coaster section. Expect aid, limited event swag and distinctive finisher awards.

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.

Brave winter woods with Tour de Trails, a four race trail series around Rockford offering 3, 6, 9 and 12 mile courses on natural snowy and icy trails. Choose single races or a full series and support Rockford Road Runners community programs..

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.

Celebrate Earth Day on April 18 at Veterans Acres in Crystal Lake with scenic single track trails and rolling hills, choosing from 50K, 15 mile or 5 mile distances. Enjoy a big aid station with homemade snacks and bring a reusable bottle.