Trail Running calendar near Warrenville 2025-2026

Join the Orland Park Turkey Trot for a chip timed 2.5 mile cross country run through woods and paved paths around Village Hall. All participants get a long sleeve dri fit shirt and winners take home prize turkeys.

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 Winnetka Turkey Trot on Thanksgiving morning for a fun 5k on the Green Bay Trail with Family Trot and Speedy Trotters divisions and a rolling start. Festive vibes, kids get #1 medal and proceeds support local charities.

Join the Brooks Northeast XC Championships at Franklin Park for a day of fast cross country races for youth, high school and open runners. Enjoy swag for early registrants, championship medals and chances to qualify for the Brooks XC finals..

Join the Brooks Midwest XC Championships on Nov 29, 2025 at UW Parkside in Kenosha, WI. Multiple races award medals and offer a shot to qualify for the Brooks XC Championships in San Diego.

Chicago Gaelic Park Carraig Challenge The event is a cross country running and walking event at Chicago Gaelic Park / Carraig Irish Pub in Oak Forest, Illinois, on Sunday, November 30, 2025. Two course options are offered: 5K run 1.5 mile..

Join the Frozen Feet 5k Trail Run on January 3, 2026 at Creek Ridge County Park for a brisk two loop trail with a couple of fun hills and rooty terrain. Warm up with a complimentary winter hat and gloves and post race snacks and drinks.

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.

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 unveils a new hillier course with a Roller Coaster section to challenge trail lovers. Pick 30k 50k or new 50 mile and earn cowboy swag plus wooden medals or belt buckles.

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.

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.