Trail Running calendar near Orland Park 2025-2026

Timely Nonsense is an urban ultramarathon held at a 58-acre park in Chicago, at the intersection of California and Montrose. The course features a 0.75-mile paved loop that runners complete for the 6-hour or 12-hour timed events. An aid station at the Start/Finish provides typical ultrarunning fare,..

Half Day at the Lake is a unique ultra-running event held in Evanston, Illinois, featuring 6- and 12-hour race options. The race takes place on a scenic 2-mile loop along Chicago’s north shore lakefront path, passing through Evanston’s lakefront and Northwestern University’s campus. The course is a..

Tryon Farm 50k is one of several trail distances offered at Tryon Farm in Michigan City, Indiana. The event includes a 4-mile loop option plus an 8-mile (two loops), 25k (four loops), 50k (eight loops), and a 2-mile Fun Run/Walk. The course blends open grassy fields with single-track dirt trails and..

Limestone Rocks! 8-Hour or 4-Hour Race takes place at Limestone Park in Kankakee, Illinois. Runners choose an endurance 8-Hour or a 4-Hour option, competing on a 1.65-mile loop course. The surface is mostly crushed limestone with sections of asphalt; the course is roughly half flat and half hilly, f..

Bloomingdale Trail 5K is an annual, family-friendly running event in Chicago, Illinois. The day features a timed 5K race along with ¼- and ½-mile dashes for young runners. The event location is 1834 N Lawndale Ave, Chicago, IL 60647, and the site describes a welcoming atmosphere for runners of all a..

Anderson Humane's Walk4Animals & 5K Run takes place in Batavia, Illinois, centered at the Peg Bond Center at 100 N Island Ave along the Batavia Riverwalk. The event offers a 5K Run (timed), a 1.5-mile Walk, and a T-Shirt Only option. The Walk4Animals route is a 1.65-mile loop around the Batavia Rive..

The Fall Trail Classic 2.0 is a trail running event held at Marengo Ridge Conservation Area in Marengo, Illinois. It features two races on the same day: a 4-mile run through oak and hickory woodlands, small stream bridges, and restored prairie trails, and a 7-mile run that includes the 4-mile loop p..

Fire Zone 5k is a first-time event hosted by the Lockport Fire Foundation in Lockport, Illinois. The 5k takes place on a Forest Preserve trail, with a single full marked loop starting at the Hassert Park parking lot across from Lockport Township Fire Station Six and ending back there. Runners and wa..

Farmer Ken's Pumpkin Dash 5K takes place in Franksville, Wisconsin (53126). It is a 5K trail run along a grass/dirt path set beside corn and other farm fields, offering a scenic rural landscape. The course runs through agricultural surroundings, giving runners a scenic, rustic experience.Participant..

Des Plaines River Trail Races is an endurance trail event held in Lake County, Illinois, starting and finishing at Half Day Forest Preserve. The program features a Half Marathon, Marathon (Boston Qualifier), 50K, and 50 Mile ultra. Runners traverse a 100% trail course on a fast, flat crushed gravel..

Soul Crusher is a trail-running event in Crystal Lake, Illinois, offering 5- and 10-mile options. Runners navigate single-track forest trails through Veteran Acres and Sternes Woods, with a course described as challenging, fun, and bone-decorated. The start line sits in the middle of the park at a s..

Saw Wee Kee - Fall Trail Run is held at Saw Wee Kee Park, Sundown Lane, Yorkville, Illinois. The event is the Fall Trail Run segment of a four-race series; each race features a different course and medal piece, and completing all four earns the series medal with different seasonal swag at each stop...

The Buckley 5 Miler is a scenic and challenging cross-country trail race held at the Buckley Homestead in Lowell, Indiana. The 5-mile course features a 2-mile loop on the north side of the park followed by a 3-mile loop through the park, finishing at the pioneer farm. Runners encounter a picturesque..

Palos Park Spooky Shuffle 2025 is a 5K and 10K trail run/walk held at Swallow Cliff South Forest Preserve in Palos Park, IL, organized by the Palos Park Department of Recreation & Parks in partnership with the Forest Preserves of Cook County. Runners traverse the Sag Valley Trail System on wide, unp..

Witches in the Woods 5K/2K is a Halloween-themed running event at the Lake County Fairgrounds in Crown Point, Indiana. Participants can choose a 5K Timed Halloween Run or a Non-Timed Halloween 2K Walk. The night-time course weaves through the fairgrounds’ trees and surrounding roads, with flashlight..

Howl-o-ween 5k – Schaumburg takes place in Rolling Meadows, IL at Busse Woods. This pet-friendly 5k run/walk follows a scenic, paved, flat out-and-back Busse Woods Trail and is timed by J3 Timing with live results. The event supports animal charities, featuring Fetching Tails Foundation as a partner..

Fancy Nonsense 25k/50k is a whimsical ultramarathon organized by CUSS Running, held near Chicago at Red Gate Woods in the Palos Trail System (Willow Springs/Lemont, IL). The course is a 5.5-mile mostly runnable single-track loop, repeated to reach 25k or 50k. Expect a playful, mischievous atmosphere..

ERC John Hennelly Public Cross Country Races are held at Lovelace Park in Evanston, IL. The event features a three-lap, 3.5-mile cross-country course that weaves hills, open fields and varied terrain, offering a challenging run for individuals and teams. Races are open to runners forming teams of th..

The Grand Mere Challenge 5K is a 5K trail race in Stevensville, Michigan, starting and finishing inside Grand Mere State Park. The course blends rolling sand dunes, shaded forest singletrack, and scenic stretches along Lake Michigan, delivering a challenging yet scenic run. Runners encounter dune cl..

Bristol Woods Trail Run takes place in Bristol, Wisconsin at Bristol Woods County Park, hosted at the Pringle Nature Center (9800 160th Ave). The event offers a 5K Trail Run and a 2 Mile Walk, plus junior versions for participants 18 and under. The course runs along the park’s trails, described as a..