Trail Running calendar near Orland Park 2025-2026

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 prai..

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 Tow..

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 surround..

Experience the scenic and fast Des Plaines River Trail in Lake County, IL with Half Marathon, Marathon, 50K or 50 Mile distances starting and finishing at Half Day Forest Preserve. Flat crushed gravel and brilliant fall color make it ideal..

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, fi..

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..

Palos Park Spooky Shuffle 2025 The Palos Park Spooky Shuffle takes place Saturday, October 18, 2025, at Swallow Cliff South Forest Preserve in Palos Park, Illinois. The event offers trail distances: 5K 10K Registration includes tiered fee..

Event details The event takes place on October 18, 2025 in Crystal Lake, IL. Distances offered: 10 mile - $69.00 5 mile - $47.00 Early bird pricing is available until July 30, 2025. Registration closes October 15, 2025 at 11:59 PM CT. Ent..

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 t..

Join the Fancy Nonsense 25k or 50k for a whimsical trail ultra through Palos Trail System near Chicago, featuring runnable single track loops and full aid stations. Expect mischief, laughs, and a joyful return to the love of running.

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..

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 individu..

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, delive..

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 un..

Turkey Trails - Greater Chicago is a Thanksgiving-themed running event in Shorewood, Illinois, held at Hammel Woods Route 59 Access (554 Brook Forest Ave). It offers in-person distances of 1 mile, 5k, 10k, a Kid’s Dash, plus a Virtual Race..

The Fast Track Cross Country Open is a 3.05-mile race held in Schaumburg, Illinois, on the MacNider cross country course near Hoover Elementary School. Scheduled for November 9, 2025, it features separate women's and men's races open to all..

Event details The Big Timber XC Challenge takes place Sunday, November 9, 2025 at Camp Big Timber, Big Timber Road at Tyrrell Road, Elgin, Illinois. Distances offered: 3 miles - one loop of the perimeter trail 5 miles - two loops of the pe..

The Abominable Trail Race is an exciting autumn trail running event held annually at LG Ziplines and Adventures in Lake Geneva, Wisconsin. It features three race distances: 5K, 15K, and 30K, with the 30K available for individual runners or..

Event overview The Bigfoot Half Trail Run is scheduled for November 15, 2025 at Stoney Run County Park in Hebron, Indiana. The event is organized by Crazy Legs Race Series and Paul Stofko. The distance is Half marathon (13.1 miles) run on t..

The Forge Trail Run Festival takes place at The Forge: Lemont Quarries in Lemont, Illinois, a late‑fall Midwest trail event set among woods, gravel paths, and the historic Lemont Quarries and I&M Canal. Runners may choose from 10K, 20K (Hal..