Trail Running calendar near Orland Park 2025-2026

Lace up for the Foot Pursuit 5K at Sunset Hill County Park in Valparaiso on March 7 and tackle a scenic, wooded course with rolling hills. Finishers enjoy awards, plenty of postrace food, and a welcoming community vibe.

Muddy Shamrock at The Forge in Lemont is a scenic but technical trail race with half and quarter options over wooded single and double track, rocks, roots and mud. Chip timing, a race shirt, age group awards and a festive post race party aw..

Tombstone hits Sunset Hill Farm in Valparaiso on March 14, 2026 with 30k, 50k and a new 50 mile trail over the famed Roller Coaster hills. Expect fun swag including a cowboy hat, limited tee and medals or buckles for finishers.

False Spring Trail Runs : March 21, 2026, LaPorte, IN The event offers two distances: Half 10K Start and finish are at Soldiers Memorial Park Trailhead on Lake Shore Drive in LaPorte, IN. The 10K follows one full loop of the trail system...

Save the Drama for Your Llama is a six hour trail challenge at Luhr County Park where runners rack up as many 1.7 mile loops as possible. Run at your own pace, refuel between laps and chase the most miles in a friendly festive atmosphere.

Celebrate Earth Day on April 18 in Crystal Lake with looped trail races of 50K, 15 mile, and 5 mile on rolling single track. Friendly aid station, scenic pond start, and relaxed festival vibe for trail runners of all levels.

Childish Nonsense brings looped ultrarunning to Deer Grove Forest Preserve in Palatine IL with races from 10K to 50 mile. Expect mellow trails, multiple laps with a main aid station about every 5.5 miles, and a welcoming, inclusive communit..

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.

Push your limits at the Chicago Yeti 7 to 11 hour Endurance Run in Willow Springs, a looped trail through restored forest and rolling hills with pond views. Live lap timing and a playful aid station keep you on pace and fueled.

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.

Backyard Nonsense on June 6, 2026 invites runners to scenic trails at Richard Bong State Recreation Area with rolling hills and lakeside sections. Enjoy a welcoming community and choose timed options from 3 hour to a full 24 hour ultra.

XTERRA DINO Northern Indiana unfolds near South Bend, Indiana, at the Orchard Shores Picnic Area in North Liberty. Scheduled for June 20, 2026, the race is part of the XTERRA World Tour and offers multiple off-road formats: Full Distance Tr..

Event The Trail Golf Endurance Challenge is a trail running event at Trailyard Outpost, 2651 Clifford Rd, Valparaiso, IN. Distances offered include: 50K 10M 50K Relay 10M Relay Each Hole (route) is about 3-4 miles long. The 50K covers nin..

Event details The Oakadoke Trail Runs take place at Twin Creeks Farm, 2251 Clifford Rd, Valparaiso, IN on August 1, 2026. Registration opens March 21, 2026. Distances offered are: 18 Mile - two laps of the main loop 9 Mile - one full loop..

Event overview Chupacabra Endurance is a 10-hour running event on Saturday, August 29, 2026, at Bluhm County Park, South 1100 West, Westville, IN. Runners receive a limited-edition t-shirt and a wooden Chupacabra medal. The event references..

Run technical trails and creek crossings at the GristMill Grind, a scenic 5K and 10K in Franklin Creek State Natural Area. Challenge the hills, chase custom awards and support the Franklin Creek Conservation Association.

Timely Nonsense is a playful timed ultrarun in Chicago offering 3, 6, and 12 hour options on a roughly one mile paved loop inside a scenic 58 acre park. Hourly challenges, team relays, and a lively aid and vendor area keep the day fun for r..