Trail Running calendar near Williams Bay 2026-2027

USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve with chip timing, pacers, shuttle parking and finisher medals.

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 community run at Woodland Middle School in Gurnee on September 11, 2026, offering a 5K, 1 Mile, and a shirt only option. Proceeds support the Woodland PTA and confidential financial assistance for fees is available.

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 urban ultra at Horner Park offering 3, 6, and 12 hour options on a short paved loop. Hourly playful challenges, a single aid station, and two- or four-person relay options add variety.

A community fundraiser in Geneva with a 2.5 mile Lightning Run, a 1 mile kids race, and a Mini Road Race Rally for ages 3 to 8. Proceeds support the Geneva Park District Scholarship Fund.

A Backyard Ultra on the Rock River Parkway where runners repeat a GPS-verified 4.167-mile loop each hour until one remains. Entry is limited to 150 runners and includes an on-site aid station and crew zone.

A multi day event in Belleville WI with a Last Dot Standing format between Belleville Community Park and Dot's Tavern plus 24 and 48 hour races and long distance buckles.

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 trail ultramarathon on the Ice Age State Trail in Whitewater WI with a 55 hour time limit and nine fully stocked aid stations.

A multi-loop trail event in Dixon IL using a roughly 7.85 mile loop with distances from 8 miles to 100 miles across singletrack, meadow, and gravel surfaces.

In-person and virtual 5K, 10K and half marathon at Moraine Hills State Park with marked trails, water stations, and proceeds supporting park programs.

Experience the Bloomingdale Trail Run in Chicago featuring a timed 5K and short dashes for youth. This annual event offers a variety of distances on an urban trail for a family friendly day of running.

Timed 6 and 12 hour events on a 2 mile lakefront loop in Evanston with two aid stations, public water fountains, nearby parking, and a nonalcoholic finish beverage and finisher award.

A 10th annual farm-based 5k trail run and family day in Fort Atkinson, WI supporting A-T research with in-person and virtual participation options.

A 30 minute run or walk up Mt. Hoy in Blackwell Forest Preserve, Warrenville IL, with proceeds funding two years of housing through Bridge Communities.

Multi-hour trail running at Richard Bong State Recreation Area offering 24, 12, 6 and 3 hour options plus a backyard 24 loop format.

Join this trail event at Minooka Park featuring half marathon 10K and 5K distances. Participants can choose between running walking and rucking on a scenic course with shaded trails and a notable hill challenge.

Trail events at Rock River Heritage County Park on October 3, 2026 include a timed 5K with chip timing and a guided 2.4 mile walk, plus a park celebration with music, food trucks, tastings, and raffles.

Autumn Leaf Run is a 5K trail event at Oakdale Nature Preserve in Freeport on 10/03/2026. The looped course crosses prairies, creek and wooded trails and raises funds for park improvements through the Freeport Parks Foundation.