Trail Running calendar near Delafield 2026-2027

Push your limits at the Dawn to Dusk Endurance Run in Valders, Wisconsin, a timed trail event offering 6 to 24 hour formats on a scenic 4.5 mile lakeside loop. Live tracking and on site cabins make it an ideal weekend of endurance and camar..

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

A trail running event at Devil's Lake near Baraboo, WI on July 11, 2026, offering distances from 10K to 50 miles, marked courses with aid, post-race food and a finisher medal.

A prairie trail run and walk at Lapham Peak State Forest in Delafield supporting prairie management. The event features grass hiking and mountain bike trails, shirts for the first 100 participants, awards for run winners, and on-site regist..

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

A cross-country 5k and youth 1.6-mile event in Verona, WI on July 12, 2026, with individual and team competition, age-group and team awards, and proceeds supporting the Movin' Shoes Running Club scholarship fund.

Cliff Runner 10K on July 19, 2026 in Sherwood, WI is a 10K trail run on mostly single track with rocks, roots, boulders and over 500 feet of elevation gain. Registration includes a T shirt and finisher medal and a share of proceeds supports..

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.

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.

Thanks Sandy is a 9 mile trail run at Kohler-Andrae State Park in Sheboygan, WI. The course combines beach, boardwalk and inland trails, includes one aid station and postrun snacks with a selection of dietary options.

A Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

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.

A loop based endurance event at Busse Woods near Chicago that uses a clearly marked 3.1 mile loop over crushed limestone and gravel trails. Distances range from 5K to 50K and every completed loop counts.

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.

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.