Trail Running calendar near Libertyville 2026-2027

Experience a seasonal trail run through the natural twists and turns of Saw Wee Kee Park. Complete this bib timed race to earn a piece of the 2026 series medal and enjoy the summer landscape.

This 5K run/walk takes place on the Rock Run Greenway Trail in Joliet, starting and ending at Cemeno's Pizza. All proceeds support local cancer patients through the Pat Clark Cancer Foundation. Registration includes a T-shirt and finisher m..

Trail race at Hickory Knolls Nature Area in St Charles with 5K, 10K, and a 2 person 10K relay on June 7 2026. The course runs on dirt, grass and gravel paths with marked loops and limited on course water.

An annual trail ultra held each June with 100 mile, 100k, 50k and 38 mile options; much of the course runs on the Ice Age Trail. Registration for 2026 is by Ultrasignup lottery with a waitlist and early-invite options.

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 Spartan Trail event on a scenic segment of the Ice Age Trail near Rice Lake in Whitewater, WI. Distances include 50K, half marathon and 10K, and the trail terrain ranges from smooth to technical.

A trail event in Valparaiso, IN that scores runs like golf: runners complete hourly three to four mile "holes" and receive stroke scores. Distances include 50K, 50K Relay, 10M and 10M Relay.

Celebrating its 45th year, the YMCA Brickyard Run features a 5 Mile Gold Cup race, a 5K for younger runners, and a new 2K Family Fun Run/Walk. The event is known for its unique brick awards and supports a local YMCA scholarship fund.

Experience the natural beauty of Wolf Road Woods with 3, 6, or 9 mile trail runs on a scenic loop course. Enjoy a relaxed atmosphere featuring off road terrain and post race celebrations in the heart of the Palos Trail System.

This cross country run on July 4th in Williams Bay offers a 5K on grass trails through the Kishwauketoe Nature Conservancy. A kids' quarter-mile event is also available. Registration is online only, with awards for top age-group finishers.

Trail run and walk at Lapham Peak State Forest on July 11, 2026 supporting prairie management; first 100 participants receive a short sleeve t-shirt and run winners receive awards. Day of registration is at Lapham Lodge and a park sticker o..

A trail 5K at Byron Forest Preserve with chip timing and awards by age group, plus a 1 mile Fun Run with a participation medal. Parking and indoor restrooms are available onsite.

An outdoor obstacle course in Homewood, IL with youth and adult categories featuring 8 or 16 obstacles over 1 or 2 miles. Waves start every five minutes and finishers receive medals and t-shirts.

Experience the diverse single track trails of Valparaiso at the Oakadoke Trail Runs. Choose between 4, 9, or 18 mile courses featuring scenic creek crossings and winding switchbacks followed by a celebratory post race meal.

This 10k walk/run explores the trails of Kettle Moraine State Forest in Wisconsin. It's a cup-less event with water refills and snacks provided. A portion of donations supports The Salvation Army.

Experience a Scottish themed obstacle course race in Pingree Grove featuring 15k, 5k, and family 3k distances. Challenges include classic rigs and unique tasks like archery and caber carries in a Highland setting.

Run the Rails in Elburn, Illinois features a 1 mile fun run, a 4 mile run and a 7 mile run starting and finishing at Prairie Park on August 22, 2026. Course routes cross the Union Pacific West rail line via the Anderson Road bridge.

The Summer Trail Classic offers three distances on the single-track trails of Paul Douglas Forest Preserve. It's the third race in a yearly trail series, with proceeds supporting local trail maintenance. Participants receive a running vest..

Tough Mudder Chicago on August 29, 2026 at Rockford International Airport offers 5K, 15K and an eight hour Infinity format across fields, trails and creek crossings, with Mudder Village, finisher items, and group and volunteer options.

A 10 hour endurance run at Bluhm County Park on August 29, 2026, using a 4 to 4.1 mile loop completed on an hourly clock. Runners earn chips after four loops to trade for prizes and receive a limited edition shirt and wooden medal.