Best Things to Do in Winchester, VA

Visit Old Town Winchester: Explore the historic charm of Old Town Winchester, filled with beautifully preserved buildings, quaint shops, and delightful restaurants. Take a leisurely stroll along the pedestrian-friendly streets, browse unique boutiques, and soak in the rich history and architecture of this vibrant district.

Tour the Museum of the Shenandoah Valley: Immerse yourself in the art, history, and culture of the Shenandoah Valley at the Museum of the Shenandoah Valley. The museum showcases an impressive collection of regional artifacts, fine art, and decorative arts. Explore the beautiful gardens and enjoy rotating exhibitions and educational programs.

Discover the Shenandoah Valley Discovery Museum: Perfect for families, the Shenandoah Valley Discovery Museum offers interactive exhibits and hands-on activities that engage and educate visitors of all ages. From scientific experiments and puzzles to a climbing wall and a bubble room, the museum provides an exciting and educational experience for children.

Explore Shenandoah University: Take a stroll through the picturesque campus of Shenandoah University. Admire the beautiful architecture, visit the Shenandoah Conservatory, which hosts various performances throughout the year, and explore the Armstrong Concert Hall and Ohrstrom-Bryant Theatre for a dose of arts and culture.

Go hiking in Shenandoah National Park: Winchester serves as an excellent gateway to the stunning natural beauty of Shenandoah National Park. Lace up your hiking boots and hit the trails to explore scenic vistas, cascading waterfalls, and abundant wildlife. The park offers a range of trails suitable for all skill levels, including the popular Appalachian Trail.

Visit Belle Grove Plantation: Step back in time at Belle Grove Plantation, a historic estate that played a significant role in the Civil War. Take a guided tour of the beautifully restored mansion, stroll through the gardens, and learn about the plantation’s fascinating history. Don’t miss the opportunity to attend special events and reenactments held on the grounds.

Enjoy local wineries and breweries: Winchester is surrounded by picturesque vineyards and craft breweries. Take a scenic drive to visit wineries such as Valerie Hill Vineyard & Winery or James Charles Winery & Vineyard, where you can savor a variety of wines and enjoy the serene countryside. For beer enthusiasts, check out breweries like Winchester Brew Works or Escutcheon Brewing Co. for a taste of the local craft brew scene.

Attend a live performance: Catch a show at the Bright Box Theater or the Winchester Little Theatre, both of which showcase a variety of live performances, including plays, musicals, stand-up comedy, and live music. Enjoy a night of entertainment and support the local arts scene.

Experience history at the Stonewall Jackson’s Headquarters Museum: Delve into the Civil War history of Winchester by visiting Stonewall Jackson’s Headquarters Museum. Housed in the former headquarters of General Thomas J. “Stonewall” Jackson, the museum offers exhibits, artifacts, and displays that provide insights into the life and military career of this iconic Confederate leader.

Attend a festival or event: Winchester hosts a vibrant calendar of events throughout the year. From the Shenandoah Apple Blossom Festival, a beloved springtime celebration, to the Oktoberfest and holiday parades, there’s always something happening in Winchester. Check the local event calendar to see what exciting festivals and events coincide with your visit.

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