Things To Do
Old Town Winchester Pedestrian Mall
You could spend several hours wandering through Winchester’s Loudoun Street Pedestrian Mall. The brick-clad street boasts restaurants and shops, plus a Civil War museum, and other historic buildings. The Apple Blossom Festival, which starts in late April, is a popular 10-day celebration of spring.
Winchester-Frederick County Visitor Center
The visitor center has a lot of information about the history of Winchester along with maps of the area and a nice little recreational area where you can fish or walk their trails.
State Arboretum of Virginia
This beautiful farm preserves a diverse collection of trees and plants. Several trails and a loop drive make it easy to explore the collection and enjoy the beauty.
Handley Regional Library
This library has a beautiful exterior and interior that was designed to suggest an open book. The rotunda forms the spine and two wings are the book’s covers. It is named for Judge John Handley, whose will allocated money “to build a library” for the free use of the people of the city of Winchester forever.”
George Washington's Office Museum
Founded in the 1730s, Winchester is the oldest town in the Shenandoah Valley. George Washington developed his reputation and skill as a commander while living and working in the area. You can visit George Washington’s Office Museum to learn about his time here as he planned and oversaw the construction of Fort Loudoun. Fun fact: Though Washington spent many important years of his life in town, he was not pleased to be in Winchester and referred to it as “this vile post.”
Blackwater Falls State Park
This is where the lovely couple got engaged! It is quite a distance away but offers some awe-inspiring views and trails. Patrick proposed at the top of Lindy Point Trail! ❤️
