Trail Running calendar near Westville 2026-2027

Take on the Trail Golf Endurance Challenge at Trailyard Outpost in Valparaiso with 50K, 10M or relay teams as each loop serves as a 3 to 4 mile Hole. Enjoy golf style scoring for a playful twist on hilly singletrack.

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.

Run scenic single track trails at Twin Creeks Farm in Valparaiso with 4, 9, and 18 mile options across wooded switchbacks, bridges and creek views. All finishers get on site awards and podium prizes await top runners.

Run the Mattawan Wildcat Road & Trail 5K, a spirited course from Mattawan Elementary winding through school fields into wooded trails. All finishers get a medal and proceeds support the Mattawan Public Education Foundation and Brainstrong.

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.

Experience scenic 4 mile loops across grassy fields and single track trails at Tryon Farm, with distances from a 2 mile fun run to a 50k ultra. Proceeds support Tryon Farm Institute and the race is part of the Crazy Legs series.

Challenge yourself on rugged trails in Albion, Indiana with the Indiana Trail 100 weekend featuring 150 mile, 100 mile, and 50 mile distances. Part of the IGNITE Trail Series, this scenic ultrarunning festival rewards grit and adventure.

Run from a Half Marathon to 50K and 50 Mile on flat crushed gravel along the Des Plaines River Trail, including a Boston qualifying marathon. Friendly small race with aid stations and finisher medals, so bring your own cup.

Join Fancy Nonsense for 25k, 50k, or 5 mile trail runs through Palos Trail System near Willow Springs. Mostly runnable single track on a looped course with friendly aid stations and an inclusive vibe from CUSS Running.

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.

Join the Bigfoot Half Trail Run on November 14, 2026 at Stoney Run County Park in Hebron, IN for a scenic two-loop course across fields, trails and gravel. Enjoy on-course aid, raffle prizes and event merch in a friendly, relaxed race atmos..

The Forge Trail Run Festival in Lemont Illinois offers 10K to 60K on scenic single and double track trails around the quarries and the I&M Canal. Field capped at 400 with lap courses that call for trail shoes and self supported hydration.

Run a scenic 13.1 mile loop through Chain O'Lakes State Park at the Ignite Trail Marathon on December 12, 2026; choose one loop for the half or two for the full. Expect three aid stations, local support, and rugged trail charm.