Trail Running calendar near Naperville Park District 2026-2027

Celebrate Earth Day at Crystal Lake with 50K, 15 Mile and 5 Mile trail options on a rolling 5 mile loop around the pond. Enjoy single track, a main aid station with homemade fuel and an eco friendly vibe.

Childish Nonsense is an April trail race at Deer Grove Forest Preserve with looped distances from 10K to 50 mile. Expect playful shenanigans, regular aid at the start area, and free entries for BIPOC and LGBTQ+ runners.

Run the Great Western Half Marathon and 10K on a flat out and back limestone path along the historic Great Western Trail. Hosted by Fox River Trail Runners, this longtime race supports local mental health charities.

Take on scenic trails through Teason's Woods at Cap Sauers Holding Nature Preserve with marathon and 10 mile options on wide horse paths. Enjoy rolling hills, well stocked aid stations, limited parking and a unique wooden finisher medal.

Experience the Jennie Hamilton Memorial 5 mile trail run at Stoney Run County Park in Hebron, Indiana on May 25, 2026. Expect scenic but rugged trails with a pond crossing option, midcourse aid, and a finisher water bottle.

Celebrate the 25th anniversary 5K for Double "J" in Joliet on June 6, 2026 as participants run the Rock Run Greenway and finish at Cemeno's. Proceeds support the Pat Clark Cancer Foundation and registration includes a T shirt and 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.

Take on the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K, 10M or relay teams as each loop serves as a 3 to 4 mile Hole. Enjoy golf style scoring for a playful twist on hilly singletrack.

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.

Run scenic single track trails at Twin Creeks Farm in Valparaiso with 4, 9, and 18 mile options across wooded switchbacks, bridges and creek views. All finishers get on site awards and podium prizes await top runners.

Run the Rails in Elburn on August 22, 2026 is a community fundraiser at Prairie Park supporting the Elburn Parks Commission. Choose a 1 mile fun run, a 4 mile or 7 mile race, earn kid medals and age group awards and celebrate local parks.

GristMill Grind is a scenic yet rugged 5K and 10K trail run at Franklin Creek State Natural Area on September 5, 2026. Tackle hilly, technical trails with multiple creek crossings while supporting park conservation.

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

Experience scenic 4 mile loops across grassy fields and single track trails at Tryon Farm, with distances from a 2 mile fun run to a 50k ultra. Proceeds support Tryon Farm Institute and the race is part of the Crazy Legs series.

Join the Fall into Fall Trail 5k in Janesville on October 3 for a scenic run or walk along tree lined dirt trails. Stick around for the Fall Into Fall Heritage celebration with live music, food trucks and tastings.

Haunted Highlander Assault Trail Run offers a spooky 5k in McHenry, IL with haunted sets, animatronics and actors across timed heats. Stick around for a costume contest, bonfire, live music and food.

Join the Jaimie Cox Memorial Run in Roscoe for a scenic nature 5K or a casual 2 mile walk along Stone Bridge Trail from Roscoe Middle School. Kids get a youth tee and virtual entries help fund the Jaimie Cox Memorial Scholarship.

Fancy Nonsense is a looped trail race at Red Gate Woods near Willow Springs and Lemont, Illinois, with 50K, 25K and 5 mile options on runnable singletrack. Expect repeated 5.5 mile loops, plentiful aid and classic ultra snacks.

The Witches in the Woods 5K will take place in Crown Point on Friday 30 October 2026. You can run 5 kilometers.

Join the Bigfoot Half Trail Run on November 14, 2026 at Stoney Run County Park in Hebron, IN for a scenic two-loop course across fields, trails and gravel. Enjoy on-course aid, raffle prizes and event merch in a friendly, relaxed race atmos..