Trail Running calendar near Delafield 2026-2027

Trail marathon and half marathon at High Cliff State Park featuring technical singletrack, prairie sections and Lake Winnebago views. The event is cupless with aid stations and proceeds supporting the park.

Echo 136 is a 136-mile point-to-point ultramarathon on the Ice Age State Trail in the Southern Kettle Moraine, featuring varied trail surfaces, nine staffed aid stations, and about 11,148 ft of elevation gain.

Women only Last Woman Standing trail event on a family farm near Madison, Wisconsin. Runners repeat 1.0 to 1.25 mile loops with at least 250 ft of climb per lap until one woman remains.

A timed 6- or 12-hour event on a 2 mile lakefront loop in Evanston with two aid stations, finishers' Hop Water and handcrafted awards, and permitted pacers.

Emmy's Rustic Run is a Fort Atkinson trail run and family fun day raising funds for the A-T Children's Project, featuring a 5k, a one mile walk, kids races and virtual participation.

Experience natural dirt trails and scenic views at this Janesville event featuring a competitive 5k run and casual walk. Stay for the heritage celebration with food trucks and live music after you finish.

Explore the scenic trails and steep hills of Mirror Lake State Park with several distances available. Finish your race with refreshments and s'mores around a campfire while supporting local park projects.

An annual October run and walk at Lapham Peak with 5K and 10K distances plus a Smokey Bear Fun Run. Proceeds support Lapham Peak projects and past editions publish official race results.

Trail Run at Indian Lake takes place on Oct 3, 2026 at Indian Lake County Park. The event is cup free, includes a free kids run with no registration, and features a post race party with live music and a raffle.

Run or walk along the tree lined Oak Leaf Trail before finishing at the Oktoberfest celebration in Glendale. This event features a 5k run and a 54 yard dash with post race refreshments and festival entry.

Participate in a half marathon, 5K, or rucking event at Zachariah's Acres in Oconomowoc. Support nature based programs for children with special needs while exploring prairie trails and wildflowers.

Test your endurance at the inaugural HELIOS Ultra in the Southern Kettle Moraine Forest. Choose between 6, 12, or 20 hour timeframes as a solo runner or a relay team.

Multiple endurance trail distances on a flat, crushed gravel section of the Des Plaines River Trail, starting and finishing at Half Day Forest Preserve in Lake County, Illinois. The marathon is a Boston Qualifier and the event runs each Oct..

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.

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.

Trail races of about 5 and 10 miles through Veteran Acres and Sternes Woods in Crystal Lake, IL, with single-track trails, a cupless course, packet pickup options, and finisher medals for all distances.

An October trail run at the Black Hawk Unit of the Lower Wisconsin State Riverway, organized by volunteers. Proceeds support local conservation groups and the event posts results and photos after the run.

Experience a haunted 5k trail run in Pingree Grove featuring live actors and animatronics. Stay for the bonfire and costume contest at this unique evening event.

Celebrate Halloween and support animal shelters at this dog friendly 5k in Busse Woods. Enjoy a flat paved course with treats for both humans and leashed pets at the finish line.

Experience the historic Ice Age Trail during this autumn ultramarathon in the Southern Kettle Moraine Forest. Choose between 50k and 100k distances featuring on site branded wooden medals and scenic fall colors.