Trail Running calendar near Libertyville 2025-2026

Save the Drama for your Llama is a six hour trail run at Luhr County Park on April 4, 2026, where runners complete 1.7 mile loops to see who covers the most distance. Fun, low key and perfect for trail lovers of all paces.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Celebrate Earth Day on April 18 at Veterans Acres in Crystal Lake with scenic single track trails and rolling hills, choosing from 50K, 15 mile or 5 mile distances. Enjoy a big aid station with homemade snacks and bring a reusable bottle.

Childish Nonsense is a playful trail run at Deer Grove in Palatine offering distances from 10K to 50 miles on mostly smooth looped trails. Expect laps, an on course aid station, and plenty of shenanigans from the whimsical organizers.

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.

Run scenic horse and forest trails at Teason's Woods on May 9, 2026 with a 26.2 mile marathon or a 10 mile option. Finishers get a wooden medal and can refuel with hot chili and beer.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Join the JH Memorial 5 Mile Trail Run on May 25, 2026 at Stoney Run County Park in Hebron IN for a scenic, rugged 5 mile on park trails. Expect mud, a possible pond crossing with detour, and postrace refreshments.

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.

Challenge yourself on the scenic Kettle Moraine trails in LaGrange WI with distances from 38 miles to the full 100 miler and team relays. A largely Ice Age Trail course and Western States qualifying time make this a classic ultrarun.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Experience trail running along the scenic Ice Age Trail near Whitewater, Wisconsin, with 50K, half marathon and 10K options. Rolling hills, varied footing and lakeside views make this a rewarding challenge for trail lovers.

Join DBC Gifts of Love Community 5K in Flossmoor on June 20, 2026, for a scenic 5K at Vollmer Road Grove Forest Preserve or run the Virtual 5K. Help send backpacks, school supplies and gift cards to local homeless students.

Take on the Trail Golf Endurance Challenge in Valparaiso on June 27, 2026 at Trailyard Outpost. Choose 50K, 10 mile or relay teams and tackle looped timed holes with rolling climbs and golf style scoring that blends pace and strategy.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Tackle tree covered single track and creek crossings at Oakadoke Trail Runs in Valparaiso on August 1, 2026, with 18 mile, 9 mile, and 4 mile options for all abilities. Custom finisher awards and youth pricing make this a fun family friendl..

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

Run the GristMill Grind on September 5, 2026 at Franklin Creek State Natural Area, a hilly technical trail offering 5K and 10K routes through ravines, limestone bluffs, springs and creek crossings. Proceeds support park conservation.

Explore seven walker friendly trail races across Waukesha County and Wisconsin state parks from April to October 2026. Choose 5K 10K half marathon or ruck distances, bring reusable hydration, and chase series points into a final championshi..

The Echo 136 is a 136 mile trail ultramarathon through the scenic Kettle Moraine and Ice Age State Trail near Whitewater, Wisconsin on September 25, 2026. Expect rugged singletrack, generous aid stations and a 55 hour time limit.