Trail Running calendar near Valparaiso 2026-2027

A trail running event in Valparaiso that uses golf-style scoring across repeated three to four mile "holes". Options include 50K and 10M distances plus relays, with scores based on finishing windows and lowest cumulative strokes.

Celebrate the 45th Annual Brickyard Run on June 27, 2026 in Hobart, IN with a family 2K fun run plus timed 5K and 5 mile races along scenic streets and the Oak Savannah Trail. Collect the famous brick awards for top finishers.

Trail runs at Twin Creeks Farm in Valparaiso feature tree covered single track, switchbacks, bridge crossings and farmland views. Races include 18 mile, 9 mile and 4 mile looped courses with finisher awards and youth pricing.

Run the Rails in Elburn, IL features a 1-mile fun run/walk plus 4- and 7-mile races starting and finishing at Prairie Park, with course views from the Anderson Road bridge and chip timing for the timed events.

The Naperville Trails Half Marathon & 10K is set for September 5, 2026 in Wheaton, Illinois. Runners can choose from half marathon and 10K distances, with virtual options also available.

Looped trail races at Tryon Farm feature 2 mile, 4 mile, 8 mile, 25k and 50k options across grass, single-track dirt and short pavement sections. The event supports the Tryon Farm Institute and is part of the Crazy Legs Race Series.

A flat, fast trail event at Half Day Forest Preserve offering Half Marathon, Marathon, 50K and 50 Mile distances on crushed gravel through forests and wetlands with aid stations, finisher medals and the Marathon as a Boston qualifier.

Trail races at Dr. T. K. Lawless County Park in Vandalia, MI on October 10, 2026 include a half marathon, 10k and 5k with a custom tech shirt and wooden engraved awards; course maps and past race media are available.

Trail ultraruns of 25K and 50K on a 5.5 mile loop at Red Gate Woods near Willow Springs. Mostly single track with staffed aid stations and a 5pm cutoff; no pacers allowed.

A Halloween night run and walk through the Lake County Fairgrounds. The event includes a timed 5K and a non-timed 2K walk, costume prizes, and entry to a festive market. Bring a flashlight for the evening course.

A looped half marathon trail race at Stoney Run County Park featuring mixed surfaces, aid stations at the start area and 3.5 mile mark, informal timing with popsicle sticks, oncourse signage, a race raffle, and event merchandise.

A trail race at The Forge in Lemont, IL on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double track trails with variable surfaces, an aid station for multi-lap races, and a 400-runner cap.