Trail Running calendar near Waukesha 2026-2027

A mixed relay in Brookfield with four 3K legs per team and an optional 6K two person relay. Entry is $25 or $20 for USATF members and proceeds support the Brookfield Central Cross Country team.

The Casual Hikers 10K will take place in La Grange on Saturday 1 August 2026. You can run 10 kilometers.

A multi-format event at Pike Lake State Park on August 1, 2026 offering distances from a 0.6 mile kids run to a 13.1 mile half marathon, with shaded trails and post-race watermelon.

Sequoit Sunrise 5K in Antioch Illinois is a community fundraiser race supporting the cross country program. The route starts and finishes at Antioch Community High School and runs through McMillen and Osmond Parks, with concessions and musi..

A continuous loop trail race at Deer Grove East Forest Preserve in Palatine IL offering 40 or 50 mile distances on a 3.1 mile loop with full aid support.

Loop-format trail event at Deer Grove East Forest Preserve offering distances from 5K to 50K plus continuous 40 mile and 50 mile challenges with central aid.

A retro 5K cross-country race by Fox River Trail Runners at Settler's Hill in Geneva. Entry fees are $10 for members and $12 for non-members, and proceeds support the course's preservation.

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

Thanks Sandy in Sheboygan, WI is a 9 mile trail run at Kohler-Andrae State Park featuring beach shoreline, trails, a boardwalk and post-race snacks.

Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.

A community 5K and a kids 1 mile fun run at Token Springs Elementary on 08/15/2026. The mostly bike-path out and back course runs through The Reserve neighborhood and supports the Sun Prairie West Cross Country Team.

Trail races at New Glarus Woods State Park on August 15, 2026 include 16K, 8K, 5K and a free 1K kids run. Proceeds benefit Friends of New Glarus Woods State Park and awards include age-group prizes plus a 16K consistency award.

A community cross country style event at Lussier Stadium in Madison featuring a 5 km run and a 1 mile walk; established as a memorial and serving as a fundraiser for LaFollette High School middle school feeder schools.

Loop based endurance event at Busse Woods on August 15, 2026 offering repeated 3.1 mile laps over smooth crushed limestone and packed gravel. Distances range from 5K to 50K with a central aid station and open loop format.

Continuous 3.1 mile loop at Busse Woods near Elk Grove, IL offering 40 and 50 mile options with a fully stocked aid station every lap and a 12 hour cutoff. Runs alongside The Next Loop series but is scored separately.

Participate in the annual Kettle Klomp featuring a 5k run and a 2 mile walk on a scenic cross country course. This community event supports the local high school cross country team and offers awards for various age groups.

Multi-hour looped trail challenges at Blackhawk Ski Club in Middleton, WI, with individual and team relay options, plus a 1.7 mile fun run that highlights the course features and terrain.

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve with water stations, age group awards and CAMBr as beneficiary.

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm offers 5K and 15K obstacle courses, an 8 hour Infinity option, and Mudder Village with food, music and finisher items.

Continuous 40 and 50 mile loop race at Half Day Forest Preserve with 3.1 mile laps, stocked aid each lap, crew access, and a 12 hour limit.