The Skippo Trail Race
Ballwin, Missouri, United States
Oct 31-Nov 1, 2026 - Saturday to Sunday
10k, 30k, Half-marathon
Race Information
The Skippo began in 2009 as a 20k trail race in beautiful Castlewood State Park that featured two 10k loops on a fairly flat course except, of course, for the famous stairs! The race was named after local trail running legend Skip “Skippo” MacDowell who has dedicated countless volunteer hours to maintaining the trails at Castlewood State Park. At Skip’s urging and wanting to involve as many runners as possible both beginner and seasoned, two more options were added, the 10k and the 30k, and making a weekend of the event with events on Saturdays and Sundays. The Skippo now offers something for everyone!
Related Events
The Skippo Trail Race
Date: Oct 31-Nov 1, 2026 - Saturday to Sunday
Size: 500 - 1,000 participants
Location: Ballwin, Missouri
Wild in the Woods 5 Mile and 10 Mile Trail Race
Date: Dec 5, 2026 - Saturday
Size: 500 - 1,000 participants
Location: Defiance, Missouri
Castlewood Cup 15k Trail Race
Date: Jan 30, 2027 - Saturday
Size: 500 - 1,000 participants
Location: Ballwin, Missouri
Innsbrook Half-Marathon and 10k
Date: Oct, 2027 (TBD)
Size: 500 - 1,000 participants
Location: Innsbrook, Missouri
👍 Run Pick of the Month: SKECHERS Hot Chocolate Run - St. Louis
📍St. Louis - Sunday December 6, 2026
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😄 Why We Like This Run
✅ Exclusive SKECHERS Hot Chocolate Run Fleece
✅ Chocolate Fondue Finisher’s Mug
✅ Free Race Photos
St. Louis, it’s time to lace up and get ready for the sweetest challenge of the year! The SKECHERS Hot Chocolate Run is returning to the heart of the Gateway City and you'll want you to be part of the magic. From the iconic architecture of Union Station to the vibrant energy of the Soulard area and Ballpark Village, there’s no better way to tour the city - all fueled by the chocolate at the finish line.
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Race Facts
Race Size: 500 - 1,000
Elevation: Some Hills
Course Type: Trail
Boston Qualifier: No
Kids Run: No
Where to Stay
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