Trail Running calendar near Delafield 2026-2027

A 10 km trail run at High Cliff State Park on July 19th 2026, featuring rocky single track, nearly 500 feet of climbing, and two loops of the Lime Kiln trail. Registration includes a T shirt and finisher medal and some proceeds support a lo..

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..

Continuous 3.1 miles loop race at Deer Grove East offering 40 or 50 mile options with a 12 hour cutoff. Centralized aid every lap, designated crew access, pacers allowed, and on-course medical support.

Loop-based trail event at Deer Grove East Forest Preserve in Palatine, Illinois. Distances run from 5K to 50K and each lap returns to a central aid station so athletes can decide how far to continue.

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.

A 9 mile trail run at Kohler Andrae State Park in Sheboygan with mixed surfaces including beach, boardwalk and woodland trails. Organized by TYDISH Running, the event has a single aid station and post run snacks for finishers.

A community run/walk in Brillion honoring Mike Ariens, featuring 10K, 5K and a Kids 1K on trails and downtown routes, with finish-line ice cream, commemorative bucket hats, medals, and shuttle service between venues.

A Scottish Highlander themed obstacle race in Pingree Grove Illinois offering open and competitive 5k and 15k heats plus a family 3k. Night and haunted 5k variants are offered and finishers receive a medal and t shirt.

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 running at Paul Douglas Forest Preserve with approximate 4, 9.5 and 13 mile courses on single-track trails. Part of the Dick Pond Athletics Darn Tough Trail Race Series and benefiting the Chicago Area Mountain Bikers.

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.