Discover Fall In Old Town Winchester

Where in Virginia do 200 restaurants, 5 battlefields, 4 craft breweries, Virginia’s oldest walking mall, and 19 huge apples coexist? Where does the Shenandoah Valley intersect with Patsy Cline’s final resting place? In the perfect Virginia vacation getaway: welcome to Winchester.

The heart of the entire Northern Shenandoah region, Old Town Winchester has transformed itself in the past 5 years to a vibrant cultural, shopping and dining hub while still maintaining its authenticity and small city feel, all set amongst 200+ year old limestone buildings in Virginia’s oldest walking mall.

Start your visit by discovering the newest nano breweries in the Shenandoah Valley, most within walking distance of one another. Try Alesatian, Broken Window, Escutcheon and Winchester Brew Works for unique and locally-flavored brews.

The creativity fostered by students of nearby Shenandoah University permeates the area, leading to the emergence of unique coffee shops and music venues. Well-known musicians regularly grace SU’s conservatory, and visitors can catch live performances just about every weekend throughout the year. The Summer Music Theatre program ensures world-class entertainment even when school is out of session for the summer.

Summer and fall months are prime season for the numerous farm markets and wineries in the area. Not the crowded, impersonal sites that one will find in the larger urban markets, visitors will more than likely meet and chat with an owner and share a glass or wine or sip of cider and share some stories before leaving. Try Valerie Hill and James Charles Wineries, Richard’s Fruit Market and Marker-Miller Orchard. Good luck leaving the latter without some homemade apple cider donuts!

An unexpected rainy day brings an excellent excuse to explore the history and culture of this fascinating area.

While many are aware of George Washington’s time in Charlottesville and Fredericksburg, he actually spent 10 years of his life in Winchester developing into the military and political leader he would later become. Arriving as an inexperienced and privileged 16 year old, he left 10 years later after having led the construction of Fort Loudoun during the French and Indian War. Learn his story at George Washington’s Office Museum in Old Town, and learn why there’s a statue of a pig on the lawn of the museum.

The four-story Shenandoah Valley Discovery Museum in Old Town Winchester will keep families busy for an entire afternoon, and the Museum of the Shenandoah Valley’s high quality rotating and permanent exhibits will entertain for hours. Still raining? Visitors of all ages can catch a movie at the Alamo Drafthouse Winchester, the first to be built outside of the state of Texas.


Evenings bring an opportunity to dine outside at any of over 200 restaurants in the area, and Winchester boasts the highest concentration of al fresco dining in the entire Shenandoah Valley. Or, head down to the Family Drive-In Theatre in Stephen’s City, one of only seven drive-ins left in Virginia. But get those tickets early – this very popular spot pulls visitors from all over the Northern Virginia area.

Places to Go, Things to See: