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.

Race information

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

The Corps of Discovery Trail Races, hosted by the St. Louis Track Club, take place annually in the scenic Weldon Spring Conservation Area near Saint Charles, Missouri. The event offers three distances: a 5-mile Clark Trail loop, a new 8-mile Lewis Trail loop, and a half marathon combining both trail..

The Labor Day Slay is a multi-distance running event held at Queeny Park in St. Louis, Missouri. Scheduled for August 30, 2025, it features a 5K, 10K, Half Marathon, and a 10K Ruck with 20 or 40-pound rucksacks.Participants run, walk, jog, or ruck on shaded, rolling trails starting from the Smith Pa..

The Rockin' Rockwoods 53K and 1/2 Marathon is an annual trail running event held at Greensfelder County Park in Wildwood, Missouri. The race features challenging courses on the scenic Green Rock Trail, with terrain including hard-packed dirt, loose rocks, roots, creek crossings, and steep, technical..

The DeClue Loops Trail Race is a premier trail running event held in Greensfelder Park, Wildwood, Missouri. The race features a scenic 8.2-mile loop on the DeClue Trail, starting and finishing near the park's Visitor Center. Participants can choose from multiple distances: 8 miles (1 loop), 16 miles..

The Minnie Ha Ha 12 Hour Run is a timed ultra running event held at Minnie Ha Ha Park in St. Louis, Missouri. The race features a USATF-certified, 1.17-mile paved loop course that winds through a mostly flat, wooded park with scenic views of the Meramec River and fall foliage.Participants can choose..

The Babler Bongo 15K Trail Race and 15K RUCK take place at Dr. Edmund A. Babler Memorial State Park in Wildwood, Missouri.This event features a challenging 15K loop course connecting several trails with about 1,350 feet of elevation gain, suitable for both beginners and experienced trail runners. A..