Trail Running calendar near Naperville Park District 2025-2026

Join Strong As Oak and Varsity Rush at Oakhurst Forest Preserve in Aurora on Dec 6, 2025 for 5K and 10K trail races plus kids events on mixed terrain. Hilly course, varied surfaces and finisher medals for all.

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.

Run winter single track in Crystal Lake at the Frozen Gnome on Jan 10, a Triple Black Diamond loop through Veteran Acres. Choose 50K, 10K or 50K relays for teams of 2 or 5 and warm up at the Gnome Depot with 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.

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.

Experience the False Spring Trail Runs in LaPorte, Indiana on March 21, 2026, with scenic single track, winding switchbacks, and lakeside views. Pick a 10K or a two loop half marathon, tackle rolling hills, and unwind at lively post race fe..

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.

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.

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.

Celebrate Earth Day on April 18 at Veterans Acres in Crystal Lake with scenic single track trails and rolling hills, choosing from 50K, 15 mile or 5 mile distances. Enjoy a big aid station with homemade snacks and bring a reusable bottle.

Childish Nonsense is a playful trail run at Deer Grove in Palatine offering distances from 10K to 50 miles on mostly smooth looped trails. Expect laps, an on course aid station, and plenty of shenanigans from the whimsical organizers.

The Great Western Half-Marathon & 10K will take place in St. Charles on Sunday 3 May 2026. You can run between 10 and 21 kilometers.