Join us for our annual trail race at Sherando Park—and get ready for an unforgettable fall challenge!
Now in its 7th year, this mixed-surface four-mile trail race takes runners through the paved paths and wooded trails of Sherando Park’s scenic mountain bike trail system. Whether you’re a seasoned trail runner or tackling your first off-road race, you’ll enjoy a challenging and rewarding course surrounded by crisp fall air and vibrant autumn colors.
✨ New for 2026: We’re excited to introduce a Mountain Bike Time Trial to this event! Cyclists will have the opportunity to test their speed and skills on the Sherando Park mountain bike trails in a timed, individual-start format, adding a whole new level of competition and excitement to race day.
Proceeds from all events will benefit the I’m Just Me Movement, supporting confidence, inclusion, and self-acceptance in our community.
Not up for four miles on trails?
We’ve got you covered! We’ll also offer an untimed One Mile Fun Run/Walk, perfect for participants who want to support the cause while enjoying a shorter, paved option. The one-mile course will be an out-and-back on the paved Sherando Park path, with a course marshal stationed at the turnaround. Mile participants will start just before the four-mile race.
Sep 26, 2026
Distance — 4 Miles
Type — Running
08:30
$25.00
Sep 26, 2026
Distance — 5.3 Miles
Type — Running
08:30
$25.00
Sep 26, 2026
Distance — 1 Miles
Type — Running
08:30
$15.00
These values represent the 3-year monthly averages for September in Stephens City.
Stephens City is an incorporated town in the southern part of Frederick County, Virginia, United States, with a population of 2,016 at the time of the 2020 census, and an estimated population of 2,096 in 2022. Founded by Peter Stephens in the 1730s, the colonial town was chartered and named for Lewis Stephens in October 1758. It was originally settled by German Protestants from Heidelberg.
Read more launchExplore other exciting events happening in this same region.
location_on Middleburg, Virginia, US
calendar_today Mar 22, 2026
Hand-picked events we think you’ll love.
Nov 21, 2026
The RUN Manatee 5k series offers THREE adventures to celebrate ONE community. Participants will discover Manatee County…
Read more
Nov 28, 2026
Join us for the annual Turkey Trails 5k/10k! A fun, Thanksgiving-themed event that is perfect for the whole family.The…
Read more
Dec 13, 2026
Join us for the annual Candy Cane Course 5k/12k! A fun, Christmas-themed event that is perfect for the whole family.Th…
Read more
Mar 21, 2027
WE ARE NOW OFFERING AN AQUABIKE DIVISION! Triathlon Information:Join us for the annual Space Coast Triathlon, held in …
Read more
