Castlewood Cup
Ballwin, United States • 7 Feb 2026
The Castlewood Cup is a challenging 15-kilometer trail running event held annually at Castlewood State Park in Missouri. Celebrating its 18th year in 2026, the race features a demanding course of single-track trails with varied terrain including uphills, downhills, and switchbacks, providing a true test of trail running skills. Participants enjoy a vibrant atmosphere with a 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 includes amenities such as finisher medals, sweatshirts, and live runner tracking. It is managed by Big River Race Management, a leader in race timing and event organization in the Midwest. Visit the organization's website for the most recent information.