Castlewood Cup

Castlewood Cup returns for its 18th year on January 31, 2026, at Castlewood State Park in Ballwin, Missouri. The 15-kilometer trail race courses through Castlewood’s renowned single-track, offering a scenic mix of hills, switchbacks, and occasional flat sections. As part of the Big River Trail Series, the event emphasizes classic winter trail running amid Missouri’s woods.

After the race, participants can enjoy a post-race party with BBQ, snacks, and beer (21+), plus live music when weather permits. Finisher photos/videos and live tracking are provided, adding a festive atmosphere to this challenging, scenic outing. Visit the organization's website for the most recent information.