Trail Running calendar near Williams Bay 2026-2027

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.

A trail event in Delafield, Wisconsin offering half marathon, 10K, 5K, ruck options and a Kiddos 1K; proceeds benefit Tall Pines Conservancy and courses use marked park trails.

Run the Sugar Badger 50/50 and Half in Belleville WI with 50M, 50K and half marathon options on flat, scenic Badger and Sugar River trails with trestles and a short tunnel. Aid, free photos, pizza and beer await finishers.

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.

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.

Kettle Moraine Ultramarathon in La Grange WI on June 13 and 14, 2026 showcases rugged, scenic trails with about 65 miles on the Ice Age Trail. Distances from 38 to 100 mile plus 100K and a 4 person relay; 100 mile offers a Western States qu..

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 Hawk at Blackhawk Ski Club in Middleton, WI on August 22 invites runners to chase laps on a rolling 2.25 mile loop in 3, 6, or 12 hour timed events, or enjoy the shorter Fun Run. Mixed trail surfaces, a steep climb, and team relay o..

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.

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.

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..

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.

Enjoy a scenic fall run, walk and roll through 125 acres of wooded trails, meadows and ponds. Choose a half marathon, 5K, 5K ruck or family one mile loop and support Zachariah's Acres for children with special needs.

Run from a Half Marathon to 50K and 50 Mile on flat crushed gravel along the Des Plaines River Trail, including a Boston qualifying marathon. Friendly small race with aid stations and finisher medals, so bring your own cup.

Join the Race For Open Space on Oct 11, 2026 in West Bend for a chip timed run and walk through forests, prairie and glacial moraine to benefit Cedar Lakes Conservation Foundation. Distances for all ages and awards for top finishers.

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 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.

Join Fancy Nonsense for 25k, 50k, or 5 mile trail runs through Palos Trail System near Willow Springs. Mostly runnable single track on a looped course with friendly aid stations and an inclusive vibe from CUSS Running.