Trail Running calendar near Lake Geneva 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.

A USATF-certified half marathon and 10K through Danada Forest Preserve on crushed limestone trails, finishing near the horse track. Both distances award finisher medals, with chip timing, pacers, shuttle parking, and on-course water station..

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.

A three day trail event at Rock Cut State Park featuring a night 10 km plus 25 km and 50 km races, with single race entries and Triple Crown series options that award commemorative spike prizes to finishers.

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.

Last Dot Standing runs alternating one hour 4.2 mile legs between Belleville Community Park and Dot's Tavern in Belleville WI. Parallel 24 hour, 48 hour and 8 hour events use the same course and offer mile buckles and cash prizes.

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.

A grassroots loop ultra at Dixon Park District offering 25K, 50K, 100K and 100 mile options on a 7.85 mile mixed surface loop with two aid locations, crew and pacer policies, and finisher awards.

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.

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.

Experience a chip timed 5k trail run through the diverse terrain and scenic landscapes of Oakdale Nature Preserve. All proceeds support local park projects and trail maintenance.

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.

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.