2027 The SKIPPO Trail Race

The Skippo Half Marathon returns to Castlewood State Park near St. Louis each November, a race born in 2009 from trail legend Skip 'Skippo' MacDowell's volunteer work. Now in its 17th year, the event draws about 100 runners from six states, with a loyal core—26 percent return year after year. It's a community-driven affair with a weekend festival feel, offering 10K and 30K options alongside the half.

The half-marathon course winds through Castlewood's wooded trails, largely flat but punctuated by the park's infamous stone stairs—a signature challenge that gives this race its character. Runners tackle a single loop or two shorter circuits depending on the configuration, with roots, rocks, and shade keeping it pure trail. The atmosphere is low-key and supportive, with volunteers at aid stations and fellow runners cheering each other on.

After crossing the finish line, participants collect a long-sleeve tech tee and celebrate with fellow runners. The Skippo's small size and consistent quality have made it a cherished fixture in the St. Louis trail scene, a race that honors its namesake and the trails he built.