Trail Running calendar near Naperville 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..

Experience the natural beauty of St. Charles at the Hickory Knolls Trail Run, featuring 5K, 10K, and relay options on scenic grass and dirt forest pathways.

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 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.

Test your strength and endurance at this outdoor obstacle course in Homewood. Choose between one or two mile distances featuring tire flips and spear throws to earn your finisher medal.

An endurance loop event at the Pinetum in Lowell Park, Dixon IL, using a 0.411 mile paved loop. Participants choose 6 hour, 12 hour, or 24 hour formats and track their own laps with tents allowed in the loop center.

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.

A night trail event in Dixon, IL with looped courses of about 5 miles per lap, options for single runners or three‑person relays, on mixed grass, gravel, and dirt trails.

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.

Experience the scenery of Elburn at Run the Rails featuring 1-mile, 4-mile, and 7-mile courses. Cross the Union Pacific West rail line and enjoy unique views of the Illinois countryside.

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.

Test your stamina at Bluhm County Park with this unique elimination style trail race. Complete a four mile loop every hour to stay in the running and compete for the fastest final lap.

A technical trail event at Franklin Creek State Natural Area featuring 5K and 10K routes with multiple hills, limestone bluffs, creek crossings, and a rucking option. Proceeds support the Franklin Creek Conservation Association.

USATF certified half marathon and 10K on crushed limestone trails at Danada Forest Preserve in Wheaton, IL, with finisher medals, chip timing, pacers and a virtual option.