Castlewood Cup

The Great Pumpkin Run in Washington, Missouri, is hosted at Drews Dream Pumpkin Patch, with the start and finish near the YMCA at 400 Grand Avenue. The event blends a trail run and a road race, featuring uphill sections and a unique requirement: participants carry a pumpkin for the duration. It offe..

DeClue Loops Trail Race is a premier Missouri trail event held at Greensfelder Park in Wildwood. The DeClue Trail offers four distance options: 8 miles (one loop), 16 miles (two loops), a marathon (three loops), and 50K (four loops) on an 8.2‑mile loop starting and finishing near the Visitor’s Cente..

Backyard Ultra in New Town is the first annual ultra to be held in Saint Charles, Missouri, at the New Town amphitheater (3246 Rue Royale St). The event centers on a 4.17-mile loop, with a last-person-standing format requiring runners to be back at the start within the next hour to begin the next la..

The Minnie Ha Ha 6 & 12 Hour Run is an annual timed ultrarunning event held at Minnie Ha Ha Park in St. Louis, Missouri. The race features 6- and 12-hour options on 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..

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—Dogwood, Woodbine, Hawthorn, and Equestrian—with about 1,350 feet of elevation gain. It welcomes both..

The SKIPPO Trail Race takes place at Castlewood State Park’s Special Events Area in Ballwin, Missouri. It offers multiple trail distances: 10k, Half-Marathon, 30k, plus the 10k-Half Marathon Challenge and the 40k Challenge (10k and 30k). The event spans two days (November 1–2, 2025) to accommodate g..