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. 

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

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