Running Routes in and Around Winchester, Virginia

Below are some of the popular running routes in Winchester. We will continue to add to this list. 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 – Third Battle of Winchester

Mar 29, 2020 | Winchester Favorites

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.

Whittier Park - 800m

The road around Whittier Park in Winchester is a .5 mile loop, perfect for 800 meter repeats, A little different than doing track repeats. You can add this onto the Wellness Center Route if you want to add a warmup and cool down.
Whittier Park, Walker St, Winchester, VA 22601

Trooper Manion Course - 3 miles

This is the Trooper Manion 5k course. The roads around the Winchester Airport and relatively flat and nicely paved. It is an out-and-back starting and ending at the airport. 491 Airport Rd, Winchester, VA 22602

Runners Retreat 5k - 3.1 miles

This 3.2 mile route starts at Runners Retreat and runs through the streets of Winchester. Runners Retreat is located on the walking mall at 135 N. Loudoun St. Parking can be found at the Braddock Street Auto Park at 30 N Braddock St.

Runners Retreat 5k Route

Liberty 5k Course in Jim Barnett Park - 3.2 miles

This is the course for the Liberty 5k held each 4th of July in Jim Barnett Park. There is not much of a sidewalk on parts of the East Cork Street portion, but the rest of the route is on sidewalks and roads through the park and Shenandoah University. Parking can be found at the War Memorial building parking lot or at the Kiwanis Shelter. Directions to War Memorial building.

Green Circle 10k - 6.34 miles

The Green Circle runs throughout Winchester. You can access the trail at many different locations. The actual start/end of the circle is at the corner of Millwood Ave. and East Jubal Early Drive. For more info on the trail, click here.

Stephens City - 7 miles

Stephens City is a great area to run. Located just south of Winchester. There is a nice multi use trail that runs along Warrior Drive and Sherando Park has paved and trail areas to run on. This route starts in the Dunkin’ Donuts / Handymart parking lot.
760 Warrior Dr, Stephens City, VA 22655

Stephens City - 6 miles

Valley Health Winchester Medical Center - 8 miles

This route starts and ends at the Valley Health Wellness Center and winds through streets in Winchester. – 401 Campus Blvd, Winchester, VA 22601

Stephens City - 8.5 miles

Stephens City is a great area to run. Located just south of Winchester. There is a nice multi use trail that runs along Warrior Drive and Sherando Park has paved and trail areas to run on. This route starts in the parking lot across from the pool in Sherando Park.
201 Splash Ave, Stephens City, VA 22655

Stephens City - 9 miles

Stephens City is a great area to run. Located just south of Winchester. There is a nice multi use trail that runs along Warrior Drive and Sherando Park has paved and trail areas to run on. This route starts in the parking lot across from the pool in Sherando Park.
201 Splash Ave, Stephens City, VA 22655

Echo Loop - 10.2 miles

The Echo Loop gets its name from Echo Lane, which is part of this large loop. You start and end at Handley High School – 425 Handley Blvd, Winchester, VA 22601

Echo 10 Miler

Red Bud - 13.31 miles

This route uses part of the Third Battle of Winchester Battlefield and the surrounding roads to stretch out a nice long run.
Start at Millbook High School – 251 First Woods Dr, Winchester, VA 22603

Looking for longer running routes near Winchester, Virginia?

W&OD Trail

Western Maryland Rail Trail

C&O Path – (access in Harper’s Ferry)