Castlewood Cup

The Castlewood Cup is an annual 15-kilometer trail running event held at Castlewood State Park in Ballwin, Missouri. Celebrating its 18th year in 2026, the race features a challenging course of Castlewood’s finest single-track trails, including uphills, downhills, and switchbacks, providing a true test of trail running skills. Participants enjoy a vibrant atmosphere with wave starts and a festive post-race party offering BBQ, local craft beer (for those 21+), and live music, weather permitting.

The event is part of the Big River Trail Series and is managed by Big River Race Management, known for its well-organized trail races in the St. Louis area. Visit the organization's website for the most recent information.