Bootlegger Trail Run

Bootlegger Trail Run

Bootlegger Trail Run stages a winter trail 10K in Upper Creve Coeur Park in Maryland Heights, Missouri, on February 22, 2026. The event is presented as the ninth annual Bootlegger 10K and takes place near the old streetcar loop at 13219 Streetcar Drive.

The course is primarily single track with many turns, switchbacks, and scenic views overlooking the lakefront. Runners complete a 1.5 mile parade loop on Streetcar Drive to naturally sort the field by pace before entering the trail, then run a full loop counterclockwise and return to the start and finish area at the old streetcar loop. Dogs are not permitted on the course or in the race. The course notes suggest a pace of about 21 minutes per mile.

Registration includes a custom finisher beer mug. All registrants will receive a custom finisher item or medal; a commemorative long sleeve tri blend shirt is available for purchase for $20. Post race snacks and beer provided by Urban Chestnut are available at the finish. Packet pickup is offered Saturday, February 21 at Fleet Feet Des Peres from 10:00 AM to 3:00 PM and on race morning beginning at 7:45 AM at the race site near Go Ape.

Awards are given to the top three male and female overall finishers and the top three male and female in standard age groups. The top three overall finishers also receive tickets to Go Ape. Sponsors include Urban Chestnut Brewing Company, Fleet Feet, and Start 2 Finish. Visit the organization's website for the most recent information.