Enjoy the Day in Downtown Winchester, VA

During your peaceful retreat at The Inn at Vaucluse Spring, explore the surrounding region and all it has to offer! Whether you’re looking for a list of outdoor activities to enjoy in Shenandoah Valley or some attractions in nearby Front Royal, we’ve got you covered! If you’re looking for some adventures to embark upon in our neighboring town of Winchester, VA, we also have some itinerary items for you! Downtown Winchester, VA, is a fun place to spend the day shopping, dining, and exploring. Here are just a few of our favorite Winchester VA things to do!

Discover more things to do in Downtown Winchester, VA, and the other towns surroundings The Inn at Vaucluse Spring when you download our free Vacation Guide. It features some of our favorite local attractions that we know you will love visiting during your stay!

Your Guide to Exploring Downtown Winchester, VA


Historic Downtown Winchester, VA, also known as Old Town Winchester, is a great destination for wandering. As you walk around the city, you will be able to shop, dine, and learn about local history! Old Town Winchester is one of our favorite places for discovering an eclectic mix of antiques, gifts, artwork, and clothing. This 250-year-old marketplace is perfect for strolling and window shopping! The Simply Charming Boutique is a favorite of Old Town Winchester shops. This locally owned boutique features beautiful jewelry, trendy clothing, and delightful candles among other gift items. To find the perfect vacation read, we recommend sifting through paperbacks at the independent, 44-year-old Winchester Book Gallery. This charming shop also features local art, cards, and live music regularly.


Winchester, VA, shopping sure can wear you out! If you need a bite to eat, there are plenty great restaurants to enjoy. One of our favorite places for grabbing lunch during a visit to Downtown Winchester, VA, is the La Nicoise Cafe. This cozy, vintage brick cafe serves French Riviera cuisine and some amazing coffee and desserts. Soups, sandwiches, and wine are a few things you can enjoy at this premier choice of Winchester, VA, restaurants. For a variety of 50 craft beers and 50 burgers in an industrial chic setting, enjoy lunch at the 50/50 Taphouse. You can also enjoy a round of pool or game of shuffleboard here. Or, for some housemade salsa and mouthwatering carnitas, you can try El Centro Classic Mexican Food and Drink in the center of Downtown Winchester, VA. There is also a great selection of cold beer and margaritas here to enjoy on the outdoor patio.


Established in 1752, Downtown Winchester, VA, is not short on history. Here, you will discover historic cemeteries, homes, libraries, theaters, and museums! George Washington’s Office Museum is one such location. This little log building was our first president’s military office from 1755 to 1756 while Fort Loudoun was being built. The Old Court House Civil War Museum is another popular touring destination in town. Featuring a collection of over 3,000 Civil War artifacts, this museum was once used as a hospital, barracks, and prisons by both sides during the war.

Explore More on the Grounds at The Inn at Vaucluse Spring

Once your Downtown Winchester, VA, adventures are over, come back to The Inn at Vaucluse Spring for a peaceful retreat on our beautiful grounds. Don’t settle for cookie-cutter Winchester, Virginia hotels. Instead, enjoy our gorgeous bed and breakfast with forest, mill pond, and valley views that will bring you peace and rejuvenation. See you soon!