Trail Running calendar near Freeport 2026-2027

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.

Night trail races in Dixon Illinois on an approximate 5 mile loop with solo distances and a three person relay, single aid station, post race snack, and on site tees for all participants.

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 Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

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.

Run the Rails in Elburn, Illinois on August 22, 2026 features a 1-mile fun run plus 4- and 7-mile courses that start and finish at Prairie Park. The routes cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

Trail race at Paul Douglas Forest Preserve on August 23, 2026 offering approximate 4, 9.5 and 13 mile courses. Part of the Dick Pond Athletics Darn Tough Trail Race Series with proceeds benefiting Chicago Area Mountain Bikers.

Tough Mudder Chicago at Richardson Adventure Farm on August 29, 2026 combines mud and named obstacles with 5K, 15K, and Infinity lap options plus a Mudder Village festival and finisher rewards.

Trail races of 50K, 10 miles and 5 miles at Scott County Park near Long Grove, IA. The event uses a roughly 10 mile loop, has stocked aid stations, and allows pacers for the 50K with online registration only.

A technical trail event at Franklin Creek State Natural Area offering 5K and 10K courses with multiple creek crossings and forested, hilly terrain. Proceeds benefit the Franklin Creek Conservation Association.

A 5K and 10K trail run through 170 acres of restored prairie and oak savanna in Verona, Wisconsin. Proceeds support Prairie Moraine Friends and amenities include restrooms, aid stations, refreshments, and a takeaway gift.

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.

An alternating last person standing format between Belleville Community Park and Dot's Tavern, with each leg covering 4.2 miles and runners alternating until one remains. Separate 24 and 48 hour races offer distance buckles and finishers aw..

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.

A dog friendly untimed 2K and 5K trail run or walk at Case Creek Valley on September 20, 2026. Proceeds support Rock Island County Animal Care and Control and finishers receive a dog tag and treats.

A coffee themed 2K and 5K fun run at Case Creek Trails on September 20, 2026. The untimed route goes through pastures and woodlands, includes hot drinks and refreshments, and supports the Rock Island County Animal Care and Control Shelter.

Echo 136 is a 136-mile trail event on the Ice Age State Trail in Whitewater, WI, featuring varied trail types and nine staffed aid stations. Participants have 55 hours to complete the course and should follow event policies for crews and eq..