Winchester Running routes

Explore Winchester by running some of our favorite loops through Old Town and surrounding regions! These routes include some rolling hills and vary from 2-6 miles.

Downtown Run – 2 Miles

Start at Runners’ Retreat
Left onto N. Loudoun St. (0.9 mile)
Left on W. Oates Ave. (0.2 mile)
Left on Pennsylvania Ave. (0.1 mile)
Right onto W. Commercial St. (~0.05 mile)
Left onto Fairmont Ave. (0.6 mile)
Left onto W. Piccadilly St. (0.2 mile)
Right onto downtown mall (~0.06 mile)
Finish at Runners’ Retreat

Actual distance: 2 miles

Downtown Run – 3 Miles

Start at Runners’ Retreat
Left onto N. Loudoun St. (~0.06 mile)
Left onto W. Piccadilly St. (0.2 mile)
At the top of the hill veer left onto W. Piccadilly St. (~0.08 mile)
Left onto Morgan St. (~0.08 mile)
Right onto Amherst St. (0.3 mile)
Right onto Whittier Ave. (0.6 mile)
Left onto Fox Dr. (0.3 mile)
Left onto Amherst St. (0.9 mile)
Left onto Morgan St. (~0.08 mile)
Right onto W. Piccadilly St. (0.3 mile)
Right onto downtown mall (~0.06 mile)
Finish at Runners’ Retreat

Actual distance: 3 miles

Fort Collier Loop – 4 Miles

Start at Runners’ Retreat
Left onto N. Loudoun St. (1.2 miles)
Right onto Brooke Rd. (0.5 mile)
Right onto Fort Collier Rd. (1.2 miles)
Right onto Berryville Ave. (0.6 mile)
Cross North Pleasant Valley Rd.
Continue on National Ave. (0.4 mile)
Left on East Ln. (0.05 mile)
Right onto E. Piccadilly St. (0.2 mile)
Left onto downtown mall (~0.06 mile)
Finish at Runners’ Retreat

Actual distance: 4.25 miles

Fox Drive Loop – 5 Miles

Start at Runners’ Retreat
Left on N. Loudoun St. (~0.06 mile)
Left onto W. Piccadilly St. (0.2 mile)
At the top of hill veer left onto W. Piccadilly (~0.08 mile)
Left onto Morgan St. (~0.08 mile)
Right onto Amherst St. (1.2 miles)
Left on Meadow Branch Ave. (1.2 miles)
Stay Straight on W. Jubal Dr. (0.6 mile)
Turn Left on Valley Ave. (0.8 mile)
Continue straight on S. Braddock St. (0.5 mile)
Right on W. Boscawen St. (~0.08 mile)
Left on N. Loudoun St. (0.1 mile)
Finish at Runners’ Retreat

Actual distance: 5 miles

John Kerr Loop – 5 Miles

Start at Runners’ Retreat
Left on N. Loudoun St. (~0.1 mile)
Left onto W. Piccadilly St. (0.2 mile)
Right on Fairmont Ave. (0.9 mile)
Stay straight on N. Fredrick Pike (1.2 miles)
Left on Fox Dr. (1.4 miles)
Left on Amherst St. (0.8 mile)
Right on W. Boscawen St. (0.4 mile)
Left onto downtown mall (0.1 mile)
Finish at Runners’ Retreat

Actual distance: 5 miles

Green Circle Trail – 6 Miles

Start at Hampton Inn
Head North on Millwood Ave. (0.1 mile)
Right on University Dr. (0.15 mile)
Left on bike path (0.15 mile)
Left on Lowry Dr. (0.15 mile)
Left on Opequon Ave. (0.05 mile)
Right on bike path to E. Clifford St. (0.75 mile)
Right on S. Cameron St. (~0.1 mile)
Left on E. Cork St. (~0.1 mile)
Right on N. Loudoun St. (~0.1 mile)
Left on W. Boscawen St. (0.15 mile)
Veer left on Amherst St. (0.4 mile)
Left on Meadow Branch Ave. (1.1 mile)
Straight onto W. Jubal Early Dr. (1.7 miles)
Stay straight onto E. Jubal Early Dr. (0.7 mile)
Straight to finish at Hampton Inn (0.6 mile)

Actual distance: 6.3 miles

Learn more about the trail