Trail Running calendar near Palatine 2026-2027

A short social run on trails at Tolleston Dunes followed by drinks, dinner and live music at Marina Shores Yacht Club in Portage, IN. Tickets include beer, house wine or a nonalcoholic beverage and dogs and children are welcome.

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 **5 mile** trail run at Stoney Run County Park in Hebron, IN, moved to Memorial Day 2026. The marked course includes an aid station near mile three and may feature mud and a pond crossing with a short detour.

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 donut-themed family run and walk on May 30, 2026 at Kankakee Community College supporting Catholic Charities. Options include a 5K, a 2K, and a virtual participation option; youth entries are free.

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.

A trail running event at Saw Wee Kee Park in Yorkville on June 6, 2026. The soft, twisting path is bib timed with staggered starts and is part of a four run series that awards pieces of a 2026 medal and seasonal swag.

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.

A trail race at Hickory Knolls Nature Area offering 5K, 10K and a 10K two person relay on marked dirt grass and gravel paths; proceeds support the St Charles Park Foundation.

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 race on June 20, 2026 at Rice Lake Nature Trail in Whitewater, WI, using a scenic out and back section of the Ice Age Trail. The route offers three distances and varying trail surfaces from smooth to technical.

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.

A trail run and walk at Lapham Peak State Forest on July 11, 2026, raising funds for prairie management; events for adults and youth, first 100 registrants receive a T-shirt and run winners receive awards.

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

H-F Beast Obstacle Course Dash in Homewood, IL on July 12, 2026 features two age categories with obstacle runs. The event awards finisher medals and t shirts and includes an optional prep course in June.

An overnight loop endurance event at Lowell Park in Dixon, IL where participants repeat a .411 mile paved loop for 6, 12, or 24 hours. Solo and three person relay options are available and the event is self supported.