Name: Revolutionary War Guided Walking and Trolley Tour of Winchester, Virginia
Start: 2026-07-01T17:15:00-04:00
End: 2026-07-04T13:00:00-04:00
Location: 20 N Loudoun St

Revolutionary War Guided Walking and Trolley Tour of Winchester, Virginia

Join amateur historian Tim Youmans for a guided walking and trolley tour of Revolutionary War sites and prominent figures in Winchester.
About this Event

Learn about the Revolutionary War era history of Winchester with this newly developed tour created especially for the 250th Anniversary of the American Revolution!

This combination walking and trolley tour focuses on sites associated with a Revolutionary War soldier or Rev War-period prominent figure. The tour will last approximately 3 hours.

WALKING TOUR

The first part is a 0.8-mile walking component traversing eight Old Town Winchester city blocks with level or gently sloped handicap accessible sidewalks. This is mostly a loop along 2 parallel historic streets (Loudoun & Cameron) with the exception of a 1-block walk to the George Washington Office Museum. Guests are never more than 4 blocks away from the starting point where the trolley is positioned for the second segment. Those who do not feel that they can walk the full 0.8-mile loop can easily “short-cut” back to the trolley-boarding spot. Good walking shoes are recommended.

TROLLEY TOUR

After the walking segment, guests board the 26-passenger trolley which takes them on a 3.3-mile leisurely ride past 27 additional sites with at least 2 locations (weather-permitting) where guests can disembark the trolley to stretch their legs and take photos. The majority of these 27 sites include an existing 18th century building and these are pointed out to riders as the trolley passes by the site or pulls over along the curb.

Dates & Times

July 1, 2026 5:15pm

July 4, 2026 10:00am

For both dates, meet on the lawn in front of the Old Frederick County Courthouse (now Civil War Museum) at 20 N Loudoun St. Tour ends at intersection of N. Cameron & Rouss Ave (very close to start point). The trolley portion of the tour will board on Boscawen Street at the intersection with Cameron Street.

Parking is available at the nearby Court Square AutoPark at the intersection of S. Cameron St and E Boscawen St. Metered street parking is FREE on July 4.

Tour is recommended for ages 12 and up.

This tour is brought to you by the Winchester-Frederick County VA250 Committee, Preservation of Historic Winchester, and the Winchester-Frederick County Historical Society.