Trail Running calendar near Chicago 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 **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.

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 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.

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.

A trail race at Twin Creeks Farm in Valparaiso, IN on August 1, 2026 offering 18 mile, 9 mile and 4 mile courses over tree-covered single-track with creek crossings. The event features finisher awards, youth pricing, and fee assistance opti..

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

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 5K chip-timed run and a 3K scavenger-hunt walk through St. Patrick's County Park featuring trail terrain, participant medallions, post-event refreshments, awards by age group, and proceeds that support park programs.

Loop format trail event at Busse Woods in Ned Brown Forest Preserve on August 15, 2026. Runners complete 3.1 mile loops on crushed limestone and packed gravel with a centralized aid station and distances from 5K to 50K.