Trail Running calendar near Sterling 2025-2026

Take on scenic, technical single track in Mines of Spain park near Dubuque, IA with a 25K or 50K double lap option. Stone steps, stream crossings and steep climbs make this a rugged and rewarding fall trail challenge.

Join Turkey Trails Greater Chicago at Hammel Woods on November 8 for family friendly 1 Mile, 5k, 10k and kids races plus a virtual option. Chip timed 5k and 10k finishers get designer shirts and medals while kids enjoy youth sized swag.

Tackle rugged trails and a fun creek crossing at the Big Timber XC Challenge in Elgin. Choose 3 mile, 5 mile or a kids fun run, enjoy pancakes and a finisher woodallion, and support local youth organizations.

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.

Join the FOLEPI River Trail Classic on Saturday, November 29, 2025 in East Peoria for a scenic, mostly downhill 4 mile run along the River Trail. Pre registrants get a technical long sleeved shirt and everyone is invited to a post race pizz..

Challenge winter single track trails at Veteran Acres and Sterne's Woods in Crystal Lake on a triple black diamond course offering 50K, 10K and relays. The 50K is five laps of a 10K loop with a warm Gnome Depot serving hot food and coffee.

Take on the 50K MASHUP SLAM, a Midwest trail series that spans eight scenic events and rewards runners who finish five races with a special finisher buckle. Top series placers earn awards at the final G.O.A.T.z or Miner 49'er event.

Take on the Triple D Winter Race in Dubuque County on January 17, 2026 with bike and run distances for every level. Organized by local volunteers, the day ends with warm food and drinks at 7Hills Brewery Event Center and prizes for top fini..

Tackle winter trails in the Fox Valley with a three part Challenge Series featuring a 5K in Batavia, 8K in Aurora and 10K in St Charles across Jan to Mar. Register single or as a bundle and earn upgraded swag for multiple races.

Tackle the middle race of the Fox Valley Winter Challenge Trail Series on Feb 21, 2026: an 8K at Oakhurst Forest Preserve with a steep sledding hill climb and twisty, rolling winter trails. Finishers get a custom medal and premium cold weat..

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.

Run the Fox Valley Winter Challenge 10K at Hickory Knolls in St. Charles on Mar 22, 2026, over mixed trails and rolling climbs to test your pace. Finishers earn winter swag and a medal, plus extra gear for completing the series.

Join the Earth Day trail run at Veterans Acres in Crystal Lake offering 50K, 15 mile and 5 mile options on a rolling 5 mile single track loop around the pond. Enjoy homemade aid station treats and a friendly, eco minded race atmosphere.

Take on rugged single track at Loud Thunder Forest Preserve with 50 mile, 50K or half marathon looped courses that pack big elevation and scenic views. Two stocked aid stations and nearby camping make for a fun, community oriented trail wee..

Join the Sugar Badger 50/50 and Half in Belleville, WI for flat, scenic out and back runs on the Badger State and Sugar River State Trails with 50 mile, 50K and half marathon options. Expect trestle bridges, a quarter mile tunnel, aid stati..

Tackle rugged trails at the GristMill Grind in Franklin Creek State Natural Area, featuring 5K and 10K routes with creek crossings, bluffs and forest canopy. All proceeds support Franklin Creek conservation and park improvements.

Test your legs on rugged, scenic loops at the Swiss Valley Trail Races with 50K, 25K and a 5.2 mile course. Enjoy creek crossings, big climbs, free camping and showers while supporting local conservation; registration opens Jan 1, 2026.

Run the scenic 104 mile Hennepin Canal State Trail from Sterling to Colona on a flat and fast all trail course. Choose 100 mile relay, 50 mile, or Mule 50K night run and earn memorable finish swag.

The Mines of Spain 100 offers 100 mile and 100 kilometer trail ultraruns on scenic loops around Dubuque's Mines of Spain. Expect rugged singletrack, steep climbs and Mississippi River views on a challenging multi loop course.