Trail Running calendar near Hebron 2025-2026

Join the 58th Dowagiac All Trail Turkey Trot on Sunday, November 23, 2025 at the Dowagiac campus for scenic trail 10K and 5K runs plus a 1K kids run. Chip timing, live results, custom shirts and awards create a festive race day.

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.

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..

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..

Frozen Feet is a 5k trail at Creek Ridge County Park in Michigan City on Jan 3, 2026, featuring two loops, a hill and rooty terrain for a fun winter challenge. Finishers receive a warm hat and gloves and post run snacks.

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.

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.

The Muddy Shamrock at The Forge offers a half and quarter trail run through scenic Lemont Quarries with rock, roots, mud and technical single track. Expect lap based routes, rustic terrain, one aid station and a fun, challenging day outdoor..

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.

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.

Run 10K, 25K, 50K or 50 Miler loops at Deer Grove Forest Preserve West in Palatine. Mostly wide non technical trails, a single aid station, pacers allowed for 50 Miler after four loops, and on course shenanigans promise a fun day.

Run scenic trails at Teason's Woods in Palos Hills on May 9, 2026 with marathon or 10 Mile options over rolling terrain and shared two way trails. Enjoy event apparel, a wooden sunflower medal for finishers, plus post race chili and beer.

Join the JH Memorial 5 Mile Trail Run on May 25, 2026 at Stoney Run Park for a rugged trail with marked turns, a water station, and an optional pond crossing. Finishers receive snacks, medals for top places, and a free water bottle.

Join XTERRA DINO Northern Indiana in South Bend on Jun 20 2026 for off road XTERRA triathlon action at Orchard Shores beach and trails. Multiple race formats and on site camping make it an ideal weekend for adventurous multisport athletes.