Castlewood Cup

Ballwin, United States • 7 Feb 2026

The Castlewood Cup is an annual trail running event that will take place for its 18th edition on February 7, 2026, at Castlewood State Park. Participants will tackle a challenging 15km course featuring a variety of terrains, including uphills, downhills, and switchbacks, making it a true test of trail running skills. After the race, attendees can enjoy a post-race celebration with BBQ, beer (for those 21 and over), and live music, creating a festive atmosphere for runners and spectators alike. The event is part of the Big River Trail Series, which encourages participation in multiple races throughout the season. Visit the organization's website for the most recent information.

Race information

Visit the organization's website for the most recent information.
Trail runs nearby

The Weldon Spring Trail Marathon and Half, organized by the St. Louis Track Club, offers runners a scenic and challenging experience through the beautiful landscapes of Weldon Spring, Missouri. Participants can enjoy a variety of terrains, including wooded areas, scenic overlooks, and wildlife encou..

The Ozark Foothills Endurance Runs is a multi-distance running event taking place in Wildwood, Missouri, from April 4 to 6, 2025. Participants can choose from various race options, including a Kids Fun Run, 100M, 100K, 50M, 50K, NIGHT 50K, 25K Ruck, Marathon, and 25K. The event emphasizes sustainabi..

The Double Chubb event in St. Louis, MO, offers participants a choice of three race distances: 50K, 25K, and 8M, set in the scenic West Tyson County Park. This trail race emphasizes a relaxed atmosphere, with an approximate 8.5-hour cutoff for all distances.Participants can pick up their race packet..

The Thunder Chicken 100K Stage Races is a three-day trail running event held at Camp Wyman in Eureka, Missouri. Scheduled for May 2-4, 2025, participants can choose to run all three stages or select individual races, including a 21-mile, 26-mile, and 25K. The courses feature challenging terrain with..

Baby Shippey is an exciting summer running event held at the Beaumont scouting property, featuring challenging trails that test participants' endurance and skills. Runners can choose between a Half Marathon (approximately 13.25 miles) and a 10K (approximately 6.25 miles), both of which include rugge..

The Dark 2 Dawn Night Trail Races, organized by Terrain Trail Runners, is an exciting overnight trail running event taking place at Indian Camp Creek Park in Foristell, MO. Participants can choose from three race options: a 10K, a 6-hour, or a 9-hour timed ultra, all set on a scenic loop course feat..