Trail Running calendar near Winnetka 2026-2027

A timed endurance trail event near Willow Springs on a 4 mile loop with single and double track, rolling hills, a signature aid station offering snacks and drinks, and a mandatory reusable cup policy.

A low-impact, no-frills running event on May 16, 2026 in Delafield, Wisconsin offering distances from a 1K kids run to a half marathon, timed by a professional crew with proceeds supporting Tall Pines Conservancy.

A spring trail event at Pringle Nature Center featuring a 5K trail run and a 2 mile fun run or hike through hilly, dirt trails; proceeds support environmental education at the nature center.

Trail Run Xtreme in Portage, IN on May 17, 2026 offers a wooded 12K and a 3K kids race on marked single track with volunteers, race shirts, awards and a post-race meal; proceeds support the Outback Trail Commission.

A chip timed *10K* trail run at The Forge Lemont Quarries featuring mostly crushed limestone surfaces, wooded scenery, competitive overall and age group awards, and a 450 participant capacity.

A multiwave obstacle course at Byron Motosports Park offering 10K, 5K, ruck, and kids divisions, with Special Forces and Endurance competitive formats and team entry packs available.

A five-mile trail run at Stoney Run County Park on May 25, 2026, with marked trails, an aid station near mile three, possible mud and a pond crossing, manual timing, and post-race refreshments.

Dirt Circus Chicago on May 30, 2026 in Crystal Lake, IL gathers the local trail running community for a social run, expo, food, raffle, and vendor booths. Two route options and a city specific t shirt preorder are available.

A timed trail event at Richard Bong State Recreation Area on June 6, 2026, featuring multiple timed options on .75 mile loops around Vern Wolf Lake, marked trails, rolling hills, and hourly on-course challenges.

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

A community 5K on June 6, 2026 in Joliet along the Rock Run Greenway Trail with start and finish at Cemeno's Pizza. Proceeds benefit the Pat Clark Cancer Foundation to support local cancer patients and families.

Trail race at Hickory Knolls Nature Area in St Charles with 5K, 10K, and a 2 person 10K relay on June 7 2026. The course runs on dirt, grass and gravel paths with marked loops and limited on course water.

An annual June endurance trail event featuring 100 mile, 100k, 50k and 38 mile options on mainly Ice Age Trail terrain. Entry for 2026 is by lottery with an ordered waitlist and early invites for rollovers and volunteers.

Experience an authentic cross country race on a purpose built grass course in Geneva Illinois. Run as an individual or part of a team on this wide professional grade venue featuring rolling terrain and a classic atmosphere.

A Spartan Trail event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 50K, half marathon and 10K, and the trail terrain ranges from smooth to technical.

A 7 km lollipop loop at Potato Creek State Park with wide, stable paths and two notable hills. The race is part of the DINO Trail Run Series and awards bonus points plus medals for overall and age group placings.

A one day trail stage race using golf style scoring where runners start each hourly hole together and aim for the lowest cumulative stroke total. Options include a 50K (nine holes) and a 10 mile course (three holes) in Valparaiso, IN.

A multi distance event at Hobart Middle School with a road and Oak Savannah Trail out and back route, computerized bib timing, and trademark brick awards across many age divisions.

Trail races at Wolf Road Woods on June 27, 2026 offer three loop choices covering 3, 6 and 9 miles with varied off-road surfaces, tiered registration fees and post-race refreshments and awards.

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.