Trail Running calendar near Shorewood 2025-2026

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 30k 50k and 50 mile is a rugged trail race at Sunset Hill Farm in Valparaiso IN featuring a new hilly course and the Roller Coaster hills. Finishers get limited edition apparel and a cowboy hat and top distances earn a belt buckle..

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.

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.

Save the Drama for your Llama 6 Hour Trail Run invites runners to log as many 1.7 mile loops as possible at Luhr County Park during a lively six hour timed challenge. All are welcome on land stewarded by Indigenous nations.

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.

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.

Run the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K or 10M loop courses and relay teams. Unique golf style scoring by Hole turns every loop into a strategic race that rewards speed and smart pacing.

Tackle scenic single track and winding trails at the Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 4, 9, and 18 mile options. Enjoy creek crossings, farmland views and a friendly post race gathering for all finishers.

Tackle rugged trails at the GristMill Grind in Franklin Creek State Natural Area, featuring 5K and 10K routes with creek crossings, bluffs and forest canopy. All proceeds support Franklin Creek conservation and park improvements.

Run scenic trails at Tryon Farm in Michigan City with distances from a 2 mile fun run to a 50k ultra. Enjoy grassy fields, single track and friendly aid stations while supporting the Tryon Farm Institute and the Crazy Legs Race Series.

Run the scenic 104 mile Hennepin Canal State Trail from Sterling to Colona on a flat and fast all trail course. Choose 100 mile relay, 50 mile, or Mule 50K night run and earn memorable finish swag.