Trail Running calendar near Portage 2026-2027

Free one day running festival in Crystal Lake celebrating local races, clubs, and brands. Pick a 4.3 or 6.8 mile social run, browse the expo, enter raffles, demo gear, and enjoy food, drinks and community fun.

A 5 kilometer run or walk in Joliet on June 6, 2026, starting and ending at Cemeno's, with proceeds benefiting the Pat Clark Cancer Foundation; registration includes a T shirt and finisher medal.

Run the DBC Gifts of Love Community 5K in Flossmoor on June 20 to provide book bags and school supplies for homeless children. Choose onsite or virtual, earn a medal and enjoy post race snacks while supporting a great cause.

A 7 km lollipop loop at Potato Creek State Park on June 20, 2026, featuring wide stable paths and two hills. The race is part of the DINO Trail Run Series and awards medals by overall and age-group placing plus bonus series points.

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.

Experience scenic trails near Naperville at the Naperville Trails Half Marathon and 10K in Wheaton, Illinois on September 5, 2026. In person and virtual entries welcome for runners of every pace.

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 5k trail event in McHenry, Illinois on October 3, 2026 with haunted sets, animatronics, and actors on course. Multiple heats and post-race activities include a costume contest, bonfire, live music, food, plus a finisher medal and shirt.

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.

A themed 5k trail event in Pingree Grove featuring multiple heats, haunted sets, animatronics, actors, and post-run activities such as a costume contest, bonfire, live entertainment and food. Entry is listed at $50 per heat.

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.

Light up the night at Witches in the Woods 5K/2K in Crown Point. Choose a timed 5K run or a fun 2K walk, enjoy costumes, live music, treats and a family friendly market among the fairground trees.

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 festival in Lemont, Illinois on November 14, 2026 offering 10K, 20K, 30K and 60K on single and double-track trails around the Lemont Quarries and the I&M Canal.