Trail Running calendar near St. Charles 2026-2027

Tackle the Frozen Feet 5k Trail Run in Michigan City on January 3, 2026 for two looped, scenic park trails with a few hills and roots to keep it interesting. All entrants get a winter hat and gloves and can enjoy snacks and drinks after the..

Frozen Gnome on Jan 10, 2026 in Crystal Lake, Illinois is a winter trail challenge through Veteran Acres and Sterne’s Woods with 10K, a Triple Black Diamond 50K and team relays. Expect hot aid, a tech shirt and finisher medal.

Join the 50K MASHUP SLAM series in Crystal Lake and across the Midwest for trail ultras including 50K, a 53K and a 9 hour timed event. Earn a finisher buckle and series awards; register by Jan 1 2026.

Run the Whitewalker Ultra 100k in Palmyra WI on January 17 to 18 2026, a winter trail challenge of two 50k loops from Emma Carlin campground across the Ice Age and Scuppernong trails. Limited spots remain so register by January 16.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

Run a winter trail 5K at Dick Young Forest Preserve in Batavia on Jan 24, the first of three races in the Fox Valley Winter Challenge. Trails may be snowy or muddy; finishers get snacks, a medal and a cozy winter hat.

Run the Frozen Tundra IPA 5K along the Des Plaines River Trail, then warm up at Half Day Brewing with music, beer, hot toddies and food. Limited to 300 runners, entries include shirts, medals and a lively post race party.

Yeti Trail Half at Bluhm County Park in Westville, IN offers a rugged half on four rooty single track loops for trail lovers. Participants get a limited edition long sleeve shirt and winter hat and gloves while supplies last.

Run the Fox Valley Winter Challenge 8K on Feb 21 at Oakhurst Forest Preserve in Aurora, a mixed terrain winter trail with possible snow, ice, or mud. All finishers get a medal and completing the series earns bonus gear including a hooded zi..

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

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 offers 30k, 50k and 50 mile on March 14, 2026 at Sunset Hill Farm in Valparaiso on a new mixed surface course. Expect the Roller Coaster hills, aid stations, and finisher swag like shirts, winter hats, medals and belt buckles.

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.

Run with your dog through scenic wooded single track at Lake Geneva Ziplines, choosing a 4 mile loop or an 8 mile double lap. This friendly canicross event offers water at the start area, prizes for top teams, and a finisher token.

Tour de Trails is a four race winter trail series around Rockford IL from December to March, featuring 3, 6, 9 and 12 mile routes through scenic local preserves. Expect icy, snowy conditions and a friendly community vibe supporting Rockford..

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.

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.

Tackle a scenic 4 mile loop through rolling limestone and wooded trails at St James Farm in Warrenville, IL, with roots, mud and natural single loop terrain. Enjoy a long sleeve race shirt, wood finisher medallion and lively race day atmosp..

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 at Crystal Lake with 50K, 15 Mile and 5 Mile trail options on a rolling 5 mile loop around the pond. Enjoy single track, a main aid station with homemade fuel and an eco friendly vibe.