Trail Running calendar near Roscoe 2026-2027

Experience the spring blooms at Bristol Woods County Park during this hilly trail run and hike. Support local environmental education while navigating scenic dirt paths through the Pringle Nature Center.

A chip timed 10K through mostly crushed limestone trails and wooded scenery at The Forge Lemont Quarries near Lemont, IL. Part of the Chicago Racing Circuit with overall and age group awards and a 450 runner capacity.

Rail-trail event in Belleville, WI using the Badger State Trail and Sugar River State Trail. Distances include 50 miles, 50K and a half marathon on flat, soft surfaces with trestle bridges and a quarter mile tunnel.

Test your grit at Byron Motosports Park with tactical obstacle courses ranging from 5K to 10K endurance laps. Choose from elite vest challenges, weighted rucking, or open waves designed to honor the resilience of first responders.

Join the free Dirt Circus community running festival in Crystal Lake on May 30, 2026. Choose between a 4.3-mile or 6.8-mile social group run, then enjoy a festival with food, an expo of local brands, and a raffle. Meet race directors and co..

Backyard Nonsense is a timed trail event with 24, 12, 6, and 3 hour options in the Richard Bong State Recreation Area. Run as far as you want on rolling hills near Vern Wolf Lake. The event is organized by CUSS Running, which has specific p..

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

This 5K run/walk takes place on the Rock Run Greenway Trail in Joliet, starting and ending at Cemeno's Pizza. All proceeds support local cancer patients through the Pat Clark Cancer Foundation. Registration includes a T-shirt and finisher m..

Blue Mound Trail Run on June 6, 2026 in Blue Mound State Park features 10K and 18K trail races on single-track and ski trails, and serves as a fundraiser for Friends of Blue Mound State Park.

Experience the natural beauty of St. Charles at the Hickory Knolls Trail Run, featuring 5K, 10K, and relay options on scenic grass and dirt forest pathways.

An annual trail ultra held each June with 100 mile, 100k, 50k and 38 mile options; much of the course runs on the Ice Age Trail. Registration for 2026 is by Ultrasignup lottery with a waitlist and early-invite options.

Experience an authentic cross country race on a purpose built grass course in Geneva Illinois. Run as an individual or part of a team on this wide professional grade venue featuring rolling terrain and a classic atmosphere.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

Experience the natural beauty of Wolf Road Woods with 3, 6, or 9 mile trail runs on a scenic loop course. Enjoy a relaxed atmosphere featuring off road terrain and post race celebrations in the heart of the Palos Trail System.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

Trail run and walk at Lapham Peak State Forest on July 11, 2026 supporting prairie management; first 100 participants receive a short sleeve t-shirt and run winners receive awards. Day of registration is at Lapham Lodge and a park sticker o..

An endurance loop event at the Pinetum in Lowell Park, Dixon IL, using a 0.411 mile paved loop. Participants choose 6 hour, 12 hour, or 24 hour formats and track their own laps with tents allowed in the loop center.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

A night trail event in Dixon, IL with looped courses of about 5 miles per lap, options for single runners or three‑person relays, on mixed grass, gravel, and dirt trails.

Experience a Scottish themed obstacle course race in Pingree Grove featuring 15k, 5k, and family 3k distances. Challenges include classic rigs and unique tasks like archery and caber carries in a Highland setting.