Trail Running Calendar Illinois 2025-2026

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...

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..

Oktoberfest Rotary Run is an annual fundraiser in Bloomington, Illinois, held on the third Sunday each October. The event centers at GE Park / Union Park Clubhouse (1750 GE Road) and offers a chip-timed 5K on the Constitution Trail, looping through Tipton Trails and returning on blacktop paths. A 1‑..

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..

Running with Ghouls is a Halloween-themed trail run/walk in Canton, Illinois, organized by YWCA Canton. Participants can choose a 5k or 1 mile distance, with a family-friendly atmosphere and Halloween costumes encouraged but not required. The course runs on Canton Park District trails, starting and..

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..

McNotagain Fall Trail Runs takes place at McNaughton Park in Pekin, Illinois, offering distance options: 3.5 miles, 10 miles, 30 miles, and 50 miles. In a flat Central Illinois setting, the course features the same full 10-mile loop run in reverse, providing a fresh perspective while preserving fami..

The Allerton Park Trail Run, hosted by Second Wind Running Club, takes place at Robert Allerton Park and Retreat Center in Monticello, Illinois. The event features a challenging 5.7-mile trail run along the Sangamon River, known for its hidden roots, ruts, and sharp turns, as well as a 2-mile nature..

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..

Rattlesnake Master Run for the Prairie is a community running event in Urbana, Illinois, at Meadowbrook Park. The 27th annual edition features a 10K Run, a 5K Run, and a 5K Walk, plus 5K and 10K Virtual Races for remote participants. The course circles Meadowbrook Park’s 130-acre prairie and include..

Tunnel Hill 100 & 50 Mile Runs take place in Vienna, Illinois along the Tunnel Hill State Trail. The event offers 100-mile and 50-mile distances on a crushed limestone trail, with wetlands, trestles, and a historic tunnel; the 100-mile course repeats the 50-mile loop four times, the 50-mile loop twi..

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..

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 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..

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..

On the Move for Men's Health 4-Hour Endurance Challenge takes place at Ballard Nature Center in Altamont, Illinois, on a 5K wooded trail loop with rolling hills. Runners aim to complete as many laps as possible in four hours, with breaks in the Trail Village. The race offers special divisions for we..

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..

Da Deer Run Run is an 8K cross-country trail race at Timber Pointe Nature Center in Hudson, Illinois. In its fifth year, the course features two loops through Timber Pointe, using wide double-track trails with some gravel, and nods to sections of the Run the Wood Race in October with twists. The eve..

The Pere Marquette Endurance Trail Run is a challenging 7.8-mile trail race held annually in December at Pere Marquette State Park in Grafton, Illinois. Celebrating its 35th year, the course features hilly terrain and scenic views through the park. Participants enjoy pre-race coffee and packet picku..

Set in Kickapoo State Recreation Area, Oakwood, Illinois, the Siberian Express Trail Race is a 7.45-mile, 95% trail course that winds east from the park into woodlands, featuring steep hills, creek crossings, and wildlife sightings. The event emphasizes a wintry Midwest experience, with a time limit..