Trail Running calendar near Palatine 2025-2026

Trailbreaker in Waukesha invites runners to scenic courses along Glacial Drumlin and Fox River trails, with distances from marathon to Kids 1K. New ruck events add variety while proceeds support local parks and the urban forest.

Push your pace or enjoy the trail at Save the Drama for your Llama, a six hour looped trail run at Luhr County Park. Complete as many 1.7 mile laps as you can; overall winners cover the greatest distance in six hours.

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 race each late April at Deer Grove Forest Preserve West in Palatine, Illinois. Distances from 10K to 50 mile cover rolling crushed gravel loops with a friendly community vibe and plenty of shenanigans.

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..

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.

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..

Hit scenic Ice Age Trail terrain in Whitewater Wisconsin with 10K, Half Marathon and 50K options across rolling, sometimes technical trails. Pick a distance for a relaxed summer challenge or a rugged ultra with great views.

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 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 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.

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.