Trail Running calendar near Freeport 2026-2027

The Casual Hikers 10K will take place in La Grange on Saturday 1 August 2026. You can run 10 kilometers.

Sequoit Sunrise 5K in Antioch Illinois is a community fundraiser race supporting the cross country program. The route starts and finishes at Antioch Community High School and runs through McMillen and Osmond Parks, with concessions and musi..

Experience the natural beauty of Dubuque with trail races through the Mines of Spain Recreation Area. Enjoy distances ranging from 4 miles to a half marathon followed by a post race party with brick oven pizza and local beer.

A scenic 5K trail run through the restored prairies of White Oak Savanna in Dodgeville, WI, held August 8, 2026, with on-course hydration, official timing, post-run breakfast, and the option to join festival activities including live music..

A nighttime trail event in Dixon IL with looped courses including 15 mile, 10 mile, 5 mile and a three person relay. The course mixes grass, gravel and dirt and features a single aid station at the start finish.

A multi-event day in Coal Valley with a 5K Mud Adventure Run, a Ninja Kids Run, and a Cross Country Trail Run. Main obstacles include a Tire Wall, Ninja Scaling Wall and Weight Lift; spectator entry is $7.

A retro 5K cross-country race by Fox River Trail Runners at Settler's Hill in Geneva. Entry fees are $10 for members and $12 for non-members, and proceeds support the course's preservation.

Awarded OCR Buddy People's Choice, Highlander Assault in Pingree Grove IL offers 3K, 5K and 15K obstacle heats plus night and haunted 5K events.

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.

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.

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve with water stations, age group awards and CAMBr as beneficiary.

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm offers 5K and 15K obstacle courses, an 8 hour Infinity option, and Mudder Village with food, music and finisher items.

ScoCo50 is a trail race at Scott County Park near Long Grove, IA offering 50K, 10 mile and 5 mile options on mixed dirt and grass trails, with aid stations, drop bag access, and limited crew and pacer allowances.

A technical trail race at Franklin Creek State Natural Area offering 5K and 10K routes with multiple creek crossings, hill terrain, and water stations. Proceeds support the Franklin Creek Conservation Association and custom awards are prese..

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 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.