The Skippo Trail Race
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The Skippo
The Skippo is a weekend trail race held at Castlewood State Park on October 31 and November 1, 2026. The event began in 2009 as a 20k comprised of two 10k loops on a mostly flat course with a notable set of stairs on the route. The event takes place at the park's Special Events Area on Kiefer Creek Road in Ballwin, Missouri.
The race weekend offers multiple distance options and challenge combinations:
- 10K (Saturday)
- Half Marathon (Sunday)
- 30K (Sunday)
Challenge options pair the Saturday 10K with a Sunday race: a 40K Challenge (10K plus 30K) and a 10 / Half Challenge (10K plus half marathon). Challenge finishers receive a challenge-specific custom award.
Packet pickup is offered before race day at a local running store and on race weekend at the event staging area. A bag drop area is provided near the start and finish; bags should be marked for identification.
All entrants receive a custom long sleeve tech shirt. All finishers receive a Skippo mug; half marathon and 30K finishers also receive a custom medal. Top three in each 10-year age group receive custom awards. Complimentary finisher photos and videos are available. Park rules limit daily entries, and changes or refunds are restricted. Sunday courses have a cutoff time; 30K runners not starting their final loop by the published cutoff will be directed off course. Visit the organization's website for the most recent information.
