Trail Running calendar near Yorkville 2025-2026

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..

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..

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 and a Volunteer option. The course winds through Hammel Wood..

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 ages and abilities. The course consists of a short start fo..

Big Timber XC Challenge is an autumn trail race held at Camp Big Timber in Elgin, Illinois (Big Timber Road at Tyrrell Road). Runners can choose between a 3-mile Run/Walk (one loop) and a 5-mile Run (two loops), with the course featuring gravel roads, open grass, wooded paths, and a creek crossing w..

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 (Half Marathon), 30K, or 60K distances. All races share a common..

Bigfoot Half Trail Run is held at Stoney Run County Park in Hebron, Indiana. The half-marathon distance is achieved by running two loops around the park. The course includes two aid stations: one at the start/finish and a second unmanned station on the course at about 3.5 miles.All finishers receive..

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 teams of 2 to 4 in relay format. Participants navigate chall..

Orland Park Turkey Trot is a 2.5-mile chip-timed cross-country race in Orland Park, Illinois. The annual Thanksgiving morning event invites runners and walkers to traverse paved roads, paths, and wooded sections near the Village Hall, starting at the Franklin Loebe Center (14650 S Ravinia Ave). It h..

The Frozen Gnome is a challenging winter trail running event held in Crystal Lake, Illinois, at Veteran Acres park. Featuring a "Triple Black Diamond" rated course, the race offers a 50K ultra run and a 10K race, both run on a scenic 10K single-track loop through Veteran Acres and Sterne’s Woods. Th..

Muddy Shamrock @ The Forge is a trail running event held at The Forge: Lemont Quarries in Lemont, Illinois. The race offers two distances: Trail Half Marathon (about 13.1 miles, run as two laps) and Trail Quarter Marathon (about 6.6 miles, one lap) on wooded single- and double-track trails around th..

Tombstone 30k/50k/50 mile is a trail running event held at Sunset Hill Farm County Park in Valparaiso, Indiana. The lineup includes 30k, 50k, and 50-mile distances, with a new course for 2026 and a Strava link. The race is described as fun, low-key challenge with Roller Coaster hills.Aid stations ar..

The Skunk Ape 806/314 Trail Race, held at Lowell Park in Dixon, Illinois, offers challenging trail running events on March 21, 2026. Participants can choose between a 33.75-mile race to be completed in 8 hours and 6 minutes, a 13.5-mile race with a 3 hour and 14 minute limit, or a relay option. The..

The Earth Day 50k is a trail running event held in Crystal Lake, Illinois, at Veterans Acres Park. It offers three race distances: 50 kilometers, 15 miles, and 5 miles, all starting together on a 5-mile loop course featuring single track trails and rolling hills. The race emphasizes environmental re..

Childish Nonsense is a trail running event held in Palatine, Illinois, at Deer Grove Forest Preserve West. It offers multiple distances: 10K, 25K, 50K, and 50 miles, with courses consisting of laps on a mostly wide, non-technical trail. Runners encounter a single aid station at the start/finish area..

Set in Palos Hills, Illinois, the F^3 Cap Sauers Trail Marathon & 10 Mile runs through the Cap Sauers Holding Nature Preserve, the largest tract of undeveloped land in Cook County. The event offers two distances: a marathon (26.2 miles) and a 10-mile option. The course uses the Sag Valley Trail syst..