Trail Running calendar near Pingree Grove 2026-2027

A chip timed 5k at Cooper's Hawk Winery in New Lenox on May 24, 2026, limited to 500 runners and walkers. Registration includes race swag and a wine pour while the event supports the New Lenox Food Pantry.

Free one day running festival in Crystal Lake celebrating local races, clubs, and brands. Pick a 4.3 or 6.8 mile social run, browse the expo, enter raffles, demo gear, and enjoy food, drinks and community fun.

A 5 kilometer run or walk in Joliet on June 6, 2026, starting and ending at Cemeno's, with proceeds benefiting the Pat Clark Cancer Foundation; registration includes a T shirt and finisher medal.

A multi-distance trail event near LaGrange, Wisconsin on June 13–14, 2026, featuring 100% trail courses and a lottery entry system. Distances range from 50K to 100 miles and the 100 mile finish in 30 hours qualifies for Western States.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 14 June 2026. You can run between 5 and 21 kilometers.

A trail running event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 10K, half marathon and 50K on rolling hills and well established trails.

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

Celebrate the 45th Annual Brickyard Run on June 27, 2026 in Hobart, IN with a family 2K fun run plus timed 5K and 5 mile races along scenic streets and the Oak Savannah Trail. Collect the famous brick awards for top finishers.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 27 June 2026. You can run between 5 and 21 kilometers.

The Kishwauketoe Cross Country Run will take place in Williams Bay on Saturday 4 July 2026. You can run 5 kilometers.

The Wisconsin Trail Series will take place in Oconomowoc on Saturday 1 August 2026. You can run between 5 and 21 kilometers.

Run the Rails in Elburn, IL features a 1-mile fun run/walk plus 4- and 7-mile races starting and finishing at Prairie Park, with course views from the Anderson Road bridge and chip timing for the timed events.

A technical trail event at Franklin Creek State Natural Area near Franklin Grove, IL, offering 5K and 10K courses with multiple creek crossings, notable elevation changes, on-course water at key points, race shirts, and awards.

Experience scenic trails near Naperville at the Naperville Trails Half Marathon and 10K in Wheaton, Illinois on September 5, 2026. In person and virtual entries welcome for runners of every pace.

Echo 136 is a 136 mile trail event on the Ice Age State Trail in the Southern Kettle Moraine, featuring varied trail surfaces, nine staffed aid stations and a 55 hour time limit.

A looped trail event in Dixon Illinois offering 25K, 50K, 100K and 100 mile distances. The course combines singletrack, grassy meadows and gravel with two aid stations and on course crew access.

The Wisconsin Trail Series will take place in Oconomowoc on Sunday 27 September 2026. You can run between 5 and 21 kilometers.

A point to point, all trail ultramarathon along the Hennepin Canal State Trail in northwest Illinois. Multiple distances from 50K to 100 miles, with aid stations every 3 to 7 miles and a 30 hour cutoff for Western States qualification.

Run or walk the Fall into Fall Trail 5k in Janesville on October 3, a scenic timed trail through wooded dirt paths with beautiful fall views. Stay for live music, food trucks, beer and wine tasting and raffles; register by Sept 15 to guaran..

A 5k trail event in McHenry, Illinois on October 3, 2026 with haunted sets, animatronics, and actors on course. Multiple heats and post-race activities include a costume contest, bonfire, live music, food, plus a finisher medal and shirt.