Trail Running calendar near Lincolnshire 2025-2026

Join the Chicago Gaelic Park Carraig Challenge on Nov 30 in Oak Forest for a spirited cross country 5K or 1.5 mile walk at Carraig Irish Pub. Enjoy post race soup and support Gaelic Park Charities while racing for age group awards.

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.

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 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.

Kick off winter in Batavia with the Fox Valley Winter Challenge 5K, a scenic trail run across prairie, grass, and limestone that may feature snow or mud. It is the first of a three race series with connectable medals and winter swag.

The Frozen Tundra 5K will take place in Lincolnshire on Saturday 31 January 2026. You can run 5 kilometers.

Run the Cereal Killer 15k trail at Red Mill County Park in La Porte Indiana on February 7, 2026, with a four loop course through scenic woods. Enjoy quirky cereal themed post race treats, limited edition swag and a friendly community vibe.

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.

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..

Enjoy a scenic 5K trail run or walk at Sunset Hill County Park in Valparaiso on March 7, 2026, through wooded rolling hills. All ages are welcome with awards, tasty postrace refreshments, and a friendly Police and Fire challenge.

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.

Tackle muddy single and double track trails around Lemont Quarries with a trail half marathon or quarter marathon option on technical terrain. Enjoy chip timing, a race shirt and a post race party with food, beer and music.

Tackle the woodsy single track at Soldiers Memorial Park in LaPorte on March 21, 2026 with a 10K or a challenging half. Enjoy winding switchbacks, lake views, and a custom finisher award for every runner.

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.

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.

Join Trailbreaker in Waukesha for a scenic trail and road race offering distances from a marathon to a kids 1K, with ruck options and a Run Any Distance challenge. Family friendly and fundraising for local parks.

Challenge yourself at Save the Drama for your Llama, a six hour trail run at Luhr County Park in La Porte IN on April 4, 2026. Run as many 1.7 mile loops as you can and aim to cover the most miles to win overall.

The Wisconsin Trail Series will take place in Oconomowoc on Friday 10 April 2026. You can run between 5 and 21 kilometers.

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.