Trail Running calendar near Naperville 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.

A 5 mile trail run at Stoney Run County Park on May 25, 2026, featuring flagged turns, an aid station just past mile three, possible mud and a pond crossing with a short detour option, and post race refreshments.

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.

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.

A trail running event in Valparaiso that uses golf-style scoring across repeated three to four mile "holes". Options include 50K and 10M distances plus relays, with scores based on finishing windows and lowest cumulative strokes.

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

Trail runs at Twin Creeks Farm in Valparaiso feature tree covered single track, switchbacks, bridge crossings and farmland views. Races include 18 mile, 9 mile and 4 mile looped courses with finisher awards and youth pricing.

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.

The Naperville Trails Half Marathon will take place in Naperville on Saturday 5 September 2026. You can run between 10 and 21 kilometers.

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.

Looped trail races at Tryon Farm feature 2 mile, 4 mile, 8 mile, 25k and 50k options across grass, single-track dirt and short pavement sections. The event supports the Tryon Farm Institute and is part of the Crazy Legs Race Series.

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 flat, fast trail event at Half Day Forest Preserve offering Half Marathon, Marathon, 50K and 50 Mile distances on crushed gravel through forests and wetlands with aid stations, finisher medals and the Marathon as a Boston qualifier.

Join the Jaimie Cox Memorial Run on October 17, 2026 in Roscoe, Illinois for a community 5K or 2 mile walk along the scenic Stone Bridge Trail. Family friendly with kids and virtual options, supporting the Jaimie Cox scholarship.

A 5k trail event in Pingree Grove, Illinois on October 23, 2026 where participants can run, walk, or ruck through a course with haunted sets, animatronics, and actors. The evening includes multiple heats plus a costume contest, bonfire, ent..

Trail ultraruns of 25K and 50K on a 5.5 mile loop at Red Gate Woods near Willow Springs. Mostly single track with staffed aid stations and a 5pm cutoff; no pacers allowed.

Light up the night at Witches in the Woods 5K/2K in Crown Point. Choose a timed 5K run or a fun 2K walk, enjoy costumes, live music, treats and a family friendly market among the fairground trees.