Trail Running calendar near Naperville 2026-2027

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 staged trail race where runners complete scheduled 3–4 mile Holes and aim for the lowest cumulative stroke score. Distances include a nine-Hole 50K and a three-Hole 10-mile option at Creekside Trails in Valparaiso.

A multi distance event at Hobart Middle School with a road and Oak Savannah Trail out and back route, computerized bib timing, and trademark brick awards across many age divisions.

Trail races at Wolf Road Woods on June 27, 2026 offer three loop choices covering 3, 6 and 9 miles with varied off-road surfaces, tiered registration fees and post-race refreshments and awards.

Trail 5K and a children's 1/4 mile at Kishwauketoe Nature Center in Williams Bay. The grass trail course passes through hills, woods and prairie, includes a water stop, parking across the street, and awards for top finishers.

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.

H-F Beast Obstacle Course Dash in Homewood, IL on July 12, 2026 features two age categories with obstacle runs. The event awards finisher medals and t shirts and includes an optional prep course in June.

An endurance event at Lowell Park's Pinetum on a roughly 0.411 mile paved loop. Self supported 6 hour, 12 hour and 24 hour options with solo and three person relay entries and on site water and volunteer support.

Midwest trail races at Creekside Trails in Valparaiso, IN offering 4, 9, and 18 mile options over single-track, switchbacks and creek crossings. Aid stations, a cupless format, post race meal and custom finisher awards are provided.

A 10K walk/run on August 1, 2026, through the Nordic Trail System in Kettle Moraine State Forest with water refill stations, trail snacks, a cup-less policy, and donations supporting The Salvation Army.

A night trail event in Dixon Illinois offering 5 10 and 15 mile options plus a 3 person relay. Loop course over grass gravel and dirt with one aid station and a post race snack.

A continuous loop 40 or 50 mile trail race at Deer Grove East Forest Preserve in Palatine, IL. Runners repeat a 3.1 mile loop with a fully stocked aid station each lap and a 12 hour time limit.

Loop-based trail event at Deer Grove East Forest Preserve in Palatine IL offering distances from 5K up to 50K. Each lap returns to a central start area with a fully stocked aid station amid prairie, wetlands, and woods.

A community cross country event in Mount Prospect offering 1, 2 and 3 mile races. Entry is $25 and proceeds benefit the Little Giraffe Foundation.

A Scottish Highlander themed obstacle race in Pingree Grove, Illinois featuring 3K family, 5K and 15K heats with 20 to 30 obstacles, plus a torch lit night race and a haunted 5K. Spectator fee on-site is $10 and parking is free.

A loop-based trail event at Busse Woods where runners complete hourly 5K loops; each loop is timed and combined for official results, and participants decide whether to continue after each loop.

A continuous 40 or 50 mile loop race at Busse Woods on a 3.1 mile (5K) trail loop with fully stocked aid each lap and a 12 hour time limit. Personal supplies, crew zones, pacers, and on site medical staff support runners.

Run the Rails in Elburn, Illinois on August 22, 2026 offers a 1 mile fun run plus 4 mile and 7 mile courses that begin and end at Prairie Park. Courses cross the Union Pacific West rail line and benefit the Elburn Parks Commission.

Trail races of approximately 4, 9.5 and 13 miles at Paul Douglas Forest Preserve on August 23, 2026. Part of the Dick Pond Athletics Darn Tough Trail Race Series with awards, raffle prizes, and proceeds benefiting Chicago Area Mountain Bike..

Tough Mudder Chicago on August 29, 2026 at Richardson Adventure Farm features 5K and 15K obstacle runs, an 8-hour Infinity lap format, Mudder Village festival amenities, and finisher medals, shirts, headbands and drinks.