Trail Running calendar near Libertyville 2026-2027

A technical trail event at Franklin Creek State Natural Area featuring 5K and 10K routes with multiple hills, limestone bluffs, creek crossings, and a rucking option. Proceeds support the Franklin Creek Conservation Association.

Take on a scenic one mile loop at Lapham Peak with 24, 12, and 6 hour timed options or set distance goals like a marathon or 50 miles. Lighted night laps, a stocked aid station, and a welcoming club vibe make every lap count.

USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve in Wheaton, IL, with finisher medals, chip timing, pacers and a virtual option.

A timed running event on an about 1 mile paved loop in a 58 acre Chicago park, offering 3 hour, 6 hour, and 12 hour formats plus relay options and hourly on course challenges.

This obstacle course race at Indiana Dunes National Park offers three distances, including a K9 event. The course features diverse terrains inspired by military landscapes. It's open to participants aged 13 and up.

A multi-division obstacle course event at The Cliffs park featuring 5K and 10K courses, a ruck division, a multi-lap Bearded Challenge, and a kid's course. Finishers receive a shirt, medal and professional action photos.

Experience ten miles of hills and winding trails through the Byron Forest Preserve and Nardi Equine Prairie. This cup free race features cash prizes and a post race celebration with pizza at Hairy Cow Brewing Company.

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.

The Bloomingdale Trail 5K is an annual family-friendly running event in Chicago. It features a timed 5K race alongside shorter dashes for young runners. Registration is available for all three distances.

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.

A mixed-surface trail event at Tryon Farm in Michigan City featuring a 4 mile loop used for 4 mile, 8 mile, 25k and 50k distances plus a 2 mile fun run or walk, with a main station, a non-manned aid point, and parking across the street.

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.

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.

A community 5k run and walk hosted by the Lockport Fire Foundation on October 4, 2026 at Hassert Park in Lockport, IL. Entry includes a t-shirt and finisher medal for registered participants present on race day.

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.

Join this community run and walk at Vollmer Road Grove Forest Preserve to support homeless school children. Participate in person on the paved 5K trail or join virtually to help provide essential school supplies for families in need.

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.

A flat, fast trail event in Lake County on crushed gravel with 50 Mile, 50K, Marathon and Half Marathon options. The Marathon is Boston qualifying, the race is cup-less, and all finishers receive medals plus post-race food and awards.

Experience a natural trail run at Saw Wee Kee Park featuring a soft path with twists and turns. Complete this event to earn a piece of the 2026 series medal and enjoy seasonal swag in a beautiful outdoor setting.