Castlewood Cup

The Castlewood Cup is a 15-kilometer trail running event held annually at Castlewood State Park in Ballwin, Missouri. Celebrating its 18th year in 2026, the race features some of Missouri’s finest single-track trails, offering a challenging course with a mix of uphills, downhills, switchbacks, and some flat terrain. The event provides a scenic and invigorating winter trail running experience.

After the race, participants can enjoy a festive post-race party with BBQ, local craft beer (for those 21+), and live music, weather permitting. The Castlewood Cup is part of the Big River Trail Series, attracting trail runners seeking a true test of endurance and skill. Visit the organization's website for the most recent information.