Running Routes in and Around Winchester, Virginia
Looking for your next favorite route? Winchester and the surrounding Shenandoah Valley are full of scenic roads, historic trails, and peaceful park paths that make every run an adventure. Whether you’re training for your next race, enjoying a casual jog with friends, or exploring new terrain on your long run, this guide highlights some of the best spots to run in and around Winchester. Lace up RUN WINCHESTER!
These are general outlines of the routes. Please refer to a map or Google to verify street names and directions.
Please practice running safety on all routes. Some routes may not have sidewalks or shoulders.
RRCA Running Safety
WINCHESTER FAVORITES – Rose Hill Park
Rose Hill Park in Winchester, Virginia, is a hidden gem for runners seeking a serene and historically rich environment. The park offers a 1.25-mile loop trail that winds through a mix of forested areas and open fields, providing a peaceful setting for runners of all...
WINCHESTER FAVORITES – Jim Barnett Park
Spanning over 170 acres, Jim Barnett Park offers a variety of trails and pathways that cater to runners of all experience levels. Whether you’re training for your next race or enjoying a leisurely jog, this park provides a dynamic and scenic environment for your...
WINCHESTER FAVORITES – The Trails at MSV
For runners seeking a unique blend of natural beauty, art, and history, the Trails at the Museum of the Shenandoah Valley (MSV) in Winchester, Virginia, are a must-visit destination. This network of trails offers a serene escape into nature while providing a variety...
WINCHESTER FAVORITES – The Green Circle Trail
The Green Circle Trail offers a refreshing escape for runners of all levels. This scenic loop connects urban landscapes with natural beauty, providing a diverse and rewarding experience that’s perfect for your next run. Stretching approximately 6 miles, the Green...
WINCHESTER FAVORITES – Third Battle of Winchester
A favorite destination for Winchester area runners is the Third Battle of Winchester trail. If you aren’t familiar with this location, one trailhead is located behind Millbrook High School. You can find ample parking and easy trail access close to the practice football field. The trail surface is crushed gravel and dirt with just a small paved section This area includes several options for distances. I will highlight a 5 mile loop that Connor and I do periodically when we need a change of scenery.
NEARBY FAVORITES – Sherando Park
Sherando Park in Stephens City, Virginia offers a little bit of everything — quiet roads, shaded trails, open fields, and even a splash of history. Just a few miles south of Winchester, this Frederick County park is a runner’s dream, with options for both road and...