Trail Running calendar near Naperville 2026-2027

A 15k trail run at Red Mill County Park run as four marked loops. The event has a cereal theme with cereals and coffee after the race, manual timing, participant shirts or a hat and gloves if shirts sell out, and awards for overall and age..

A trail half at Bluhm County Park in Westville, IN featuring four 3.4 mile loops on single track dirt with switchbacks, manual timing, an aid station at the shelter, limited participant apparel, and a 4 hour 30 minute cut off.

An 8K winter trail race at Oakhurst Forest Preserve on February 21, 2026. The course starts with a steep sledding hill and may include snow, ice, or mud, with finish-line water, snacks, and a finisher medal.

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

A 3.1 mile all-trail run at Sunset Hill County Park in Valparaiso on March 7, 2026, with age group and overall awards, guaranteed shirts for early registrants, and a Police Fire Criminal Justice department challenge.

A trail race at Sunset Hill Farm Park on March 14, 2026 offering 30k, 50k and a new 50 mile option on a new course with prominent "Roller Coaster" hills, aid stations, time limits, and unique finishing awards and swag.

Trail races at The Forge in Lemont offer a wooded course around the Lemont Quarries with a half and quarter marathon on single and double track. Varied terrain includes gravel, rocks, mud and short technical climbs; trail shoes and personal..

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.

Woodsy single-track races at Soldiers Memorial Park in LaPorte, IN on March 21, 2026. Distances include a 10K loop and a half marathon run as two laps with a relay option; aid stations appear about every 2.5 miles and the event is cupless e..

A four-race winter trail series around Rockford, Illinois, from Dec 20, 2025 to Mar 21, 2026. Distances range from 3 to 12 miles across local forest preserves, with a series entry option available.

A 10K trail race at Hickory Knolls Discovery Center in St. Charles on March 22, 2026. Final event of a three race winter series with mixed terrain, finish line water and snacks, and finisher medals plus winter gear for series finishers.

Timed loop trail races at Lowell Park in Dixon, IL include 33.75-mile and 13.5-mile options plus a relay. Single track loops alternate direction each lap and a staffed aid station provides drinks and snacks.

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..

A six hour trail run at Luhr County Park on April 4, 2026 where participants complete as many 1.7 mile loops as possible. Course markings and lap checks determine winners by total distance covered.

Trail races in Crystal Lake, Illinois on a roughly five mile loop through single track and mixed woods. Distances include 50K, 15 Mile and 5 Mile with one main aid station, an eight hour cutoff, and age group awards.

A looped trail race at Deer Grove Forest Preserve near Palatine, IL offering 10K, 25K, 50K and 50 mile options on soft gravel loops with a single aid station per lap and inclusive entry policies.

A Batavia fundraiser for Anderson Humane featuring a timed 5K and a 1.5 mile community walk around the Batavia Riverwalk; proceeds support shelter, medical care, and wildlife rescue.

A flat out and back half marathon and 10K along the limestone Great Western Trail on May 3, 2026, hosted by Fox River Trail Runners. Registration contributions support three local mental health charities.

A trail marathon and a 10 mile race at Teason's Woods in Palos Hills on May 9, 2026, using the Sag Valley Trail. Wide horse trails, multiple aid stations, pre assigned race day packet pickup, and a unique wooden finisher medal.

Trail Run Xtreme in Portage, IN on May 17, 2026 features a wooded single-track 12K and a 3K kids race with roots, mud, and possible water crossings. Post-race shirts, a meal, and age group awards are provided.