Trail Running calendar near Bristol 2026-2027

This 5K run/walk takes place on the Rock Run Greenway Trail in Joliet, starting and ending at Cemeno's Pizza. All proceeds support local cancer patients through the Pat Clark Cancer Foundation. Registration includes a T-shirt and finisher m..

Hickory Knolls Trail Run The event is the sixth annual Hickory Knolls Trail Run & Relay. It takes place at the Hickory Knolls Nature Area within James O. Breen Community Park in St. Charles, Illinois. The event is the second installment..

Experience one of the oldest 100 mile races in the US on the scenic Ice Age Trail. This all-trail event offers distances from 38 miles to a 100 mile Western States qualifier in the heart of Wisconsin.

Experience the glacial landscapes of Wisconsin at the Whitewater Trail Challenge. Run along the historic Ice Age Trail with 10K, Half Marathon, and 50K distances starting from the scenic Rice Lake Nature Trail.

Experience the natural beauty of Wolf Road Woods with 3, 6, or 9 mile trail runs on a scenic loop course. Enjoy a relaxed atmosphere featuring off road terrain and post race celebrations in the heart of the Palos Trail System.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

This annual community event in Sun Prairie features a 5k race and a kids' fun run, with a course on neighborhood bike paths. Proceeds go directly to support the local high school cross country team.

Run the Rails offers a unique 1, 4, or 7-mile run starting from Prairie Park in Elburn. The courses cross a rail line bridge, providing views of the surrounding countryside. This community event supports the Elburn Parks Commission.

The Summer Trail Classic offers three distances on the single-track trails of Paul Douglas Forest Preserve. It's the third race in a yearly trail series, with proceeds supporting local trail maintenance. Participants receive a running vest..

Experience a flat and fast USATF certified course through the scenic crushed limestone trails of Danada Forest Preserve. Choose between a half marathon or 10k and enjoy a unique finish around a historic grass horse track.

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.

Experience a 136 mile journey along the scenic Ice Age State Trail in Wisconsin. This endurance event features diverse terrain and comprehensive aid station support over a 55 hour timeframe.

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.

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.

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.

Experience a fast and flat crushed gravel trail through the forests and wetlands of Lake County. Featuring four distances from a half marathon to a 50 mile ultra, these races offer a scenic out and back course perfect for personal bests.

Run or walk through the beautiful Fox Hill Nature Preserve this fall. Choose from trail runs, a walk, or a kids' race, all supporting local land conservation. Experience deciduous forests, restored prairies, and scenic glacial moraines.