Trail Running calendar near Delafield 2026-2027

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 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.

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.

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 at Paul Douglas Preserve offering approximate 4, 9.5 and 13 mile single-track courses as part of the Dick Pond Athletics Darn Tough Trail Race Series.

A mud obstacle event on August 29, 2026 at Richardson Adventure Farm offering 5K, 15K, timed Infinity laps, Mudder Village, and finisher rewards.

The 40/50 Mile Challenge - Half Day Forest Preserve will take place in Lincolnshire on Saturday 29 August 2026. You can run between 40 and 50 miles.

Loop based trail event at Half Day Forest Preserve where runners repeat a 3.1 mile loop, stop after any loop with no penalty, and receive official timing for each completed loop for combined results.

A 6 km cross-country race at Lovelace Park in Evanston with scholastic races, team and individual entries, race shirts, awards, and a post-race gathering with food.

Timed ultrarunning at Lapham Peak State Park with 24, 12 and 6 hour options plus a distance division for marathon and longer targets. One mile loop, chip timing, an aid station, and a cupless refill policy.

A new trail race in Verona, Wisconsin offering 5K and 10K courses through prairies, woodlands and oak savannas. Net proceeds support Prairie Moraine Friends for park restoration; parking is limited and ride sharing is encouraged.