Bootlegger 10K
Sunday, February 22nd, 2026
Take on the trails with us at our 9th annual Bootlegger 10K on Sunday, February 22nd! This winter trail race in Upper Creve Coeur Park perfectly blends nature and local lore, featuring breathtaking paths notorious for their role in the Prohibition era. Named after its reputation for gangsters, gamblers, and crime in the 1920s, the park now hosts runners, bikers, zip liners and a variety of active groups.
Bootlegger’s course is made up of primarily single-track trail with plenty of turns, switchbacks, and scenic views overlooking the lakefront. If you look closely, you might even see remnants of the Creve Coeur Lake streetcar line that brought ne'er-do-wells to the area during Prohibition! Add winter weather to the mix, and you’ll truly experience the intersection of history and adventure.
Registration includes a custom finisher item (details coming soon), and the option to purchase a commemorative long sleeve tri-blend shirt. All participants can enjoy snacks and post-race beer at the finish line!
Pricing
| Date | Through January 2nd | January 3rd - February 2nd | February 3rd - Race Day |
| Price | $25 | $28 | $31 |
*Displayed pricing does not include processing fees
Packet Pickup Information
Packet pickup details will be posted here once finalized.
Swag
All registrants will receive a custom finisher medal or item (designs coming soon) You can also choose to purchase a commemorative super soft, long sleeve tri-blend shirt during registration for just $20.
| 2026 Finisher Item Design Coming Soon |
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Course
The course is well planned with a 1.5-mile parade loop on Streetcar Drive to “naturally” sort the field by pace prior to entering the trail. Runners will complete a full loop counterclockwise and then return to the start/finish line at the old streetcar ‘loop’ building. Participants should be able to keep a pace of ~21 mins per mile. Dogs are not permitted on the course or in the race.
Awards
Custom award items will be awarded to the top three male/female overall finishers and the top three male/female in the following age groups: 19 & under, 20-29, 30-39, 40-49, 50-59, 60-69, 70+.
The top three male and female overall finishers will also receive free tickets to Go Ape!
Volunteers
Interested in volunteering? Bootlegger volunteers receive a finisher item and Fleet Feet gift card. We are looking for individuals and groups to help with packet pick-up, course marshaling, pre/post-race, and more. Please fill out the form linked below, or email barb@s2fevents.com if you're interested in volunteering.
Sponsorship & Vendors
If your business or organization is interested in sponsoring this event or being a vendor, please email barb@s2fevents.com for more information.
Contact information
- Event contact
- Jake Goldsborough
