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Top 12 Things to Do and See in Winchester, VA

June 18, 2025
Street scene of Old Town Winchester VA

Here are some of the best attractions in Winchester:

Winchester Arts & Cultural Attractions

George Washington’s Office Museum

Located in the heart of Winchester's Old Town, this small but historically significant museum is housed in a 1750s building that once served as George Washington’s office when he was a young surveyor in the region. The office is preserved as it would have appeared during Washington's time in the 1740s and 1750s, providing a fascinating glimpse into his early life before he became a national figure. Learn more at the Winchester-Frederick County Historical Society website.

Museum of the Shenandoah Valley

The Museum of the Shenandoah Valley is a must-visit for anyone interested in the rich history and culture of the region. Located in the former home of the Handley family, this museum showcases both regional art and history. It features impressive art collections, including fine art, decorative arts, and period furnishings. Exhibits also highlight the region’s Native American history, the impact of the Civil War, and the development of the Shenandoah Valley over time. Find out more at the museum’s website.

Patsy Cline Historic House

For country music fans, the Patsy Cline Historic House is an essential stop. Located in a residential neighborhood of Winchester, this modest home was where Patsy Cline, one of the most influential country singers of all time, grew up. The house has been carefully restored to reflect Cline’s childhood years, with personal artifacts, photographs, and memorabilia telling the story of her rise to fame. Learn more at the Historical Society.

Shenandoah Valley Discovery Museum

The Shenandoah Valley Discovery Museum is an interactive, hands-on museum perfect for families and children. The museum features a wide array of exhibits that encourage learning through play and exploration. Exhibits cover subjects ranging from science and technology to art and history. Kids can experiment with physics, explore the wonders of nature, and engage in creative activities. Find out about hours and tickets at the Discovery Museum website.

Stonewall Jackson's Headquarters

This historic home was the headquarters of Gen. Thomas "Stonewall" Jackson during his time in Winchester in the Civil War. The house, which dates back to the early 19th century, offers insight into Jackson’s military strategies and his impact on the city of Winchester. The site features exhibits about Jackson’s leadership during the Civil War, including his time in the Shenandoah Valley, and the broader history of the war in the region. Learn more at the Shenandoah Valley Battlefields National Historic District site.

Events & Festivals

Museum of the Shenandoah Valley Annual Garden Tour

For those who appreciate the beauty of well-maintained gardens, the Museum of the Shenandoah Valley’s Annual Garden Tour in June is a highlight. This event provides visitors with an exclusive opportunity to tour some of the area’s most beautiful private gardens. The gardens showcased in this tour vary in style, from lush, sprawling landscapes to more formal, meticulously designed spaces. Gardeners and horticulture enthusiasts can gain inspiration, learn about local flora, and discover unique gardening techniques. Learn more at the Museum website.

Shenandoah Apple Blossom Festival

One of the largest and most iconic events in Winchester, the Shenandoah Apple Blossom Festival celebrates the region’s apple-growing history. Held annually in late April or early May, the festival is a multi-day celebration with something for everyone. The highlight is the grand parade, featuring colorful floats, marching bands, and community groups. The festival also includes live music performances across various genres, arts and crafts vendors, carnival rides, and a wide array of food options. Find out about dates and tickets at the festival website.

Shenandoah Valley Music Festival

Held in the scenic surroundings of Orkney Springs, just outside of Winchester, the Shenandoah Valley Music Festival is one of the premier cultural events in the region. Taking place in late summer, this festival offers a diverse range of performances, from classical and orchestral concerts to jazz and contemporary music. The festival is a wonderful opportunity for music lovers to enjoy high-quality performances in a picturesque outdoor setting. Learn more at the festival’s website.

Parks & Outdoor Activities

Abrams Creek Wetlands Preserve

For nature lovers and those seeking tranquility, Abrams Creek Wetlands Preserve is a beautiful and serene destination. This 141-acre preserve is located just outside of Winchester and offers a network of walking trails that allow visitors to explore the area’s diverse wetlands, forests, and meadows. The preserve is home to a variety of wildlife, making it an excellent spot for birdwatching, with numerous species of migratory birds passing through, especially during the spring and fall. The preserve is administered by Winchester Parks and Recreation department.

The Winchester National Cemetery

The Winchester National Cemetery is an important and historic site, serving as the final resting place for many soldiers who died during the Civil War. Visitors can walk through the cemetery’s meticulously maintained grounds and view the graves of over 2,000 soldiers, many of whom were casualties of battles in the Shenandoah Valley. It is administered by the Shenandoah Valley Battlefields National Historic District.

Shopping & Dining

Old Town Winchester

Old Town Winchester is the charming historic heart of the city, where visitors can step back in time while enjoying modern amenities. A leisurely stroll through Old Town allows visitors to explore a variety of unique shops, cafes, and art galleries. Local boutiques offer one-of-a-kind souvenirs and artisan goods, while coffee shops and restaurants provide a perfect place to relax and enjoy a meal. Browse their website to find out more.

Winchester Brew Works

For craft beer enthusiasts, Winchester Brew Works is a must-visit stop. This local brewery, located in the heart of downtown Winchester, offers a rotating selection of high-quality beers made right on-site. Whether you’re into light, crisp ales or bold, flavorful stouts, Winchester Brew Works has something to suit every palate. The brewery features a relaxed and welcoming atmosphere with friendly staff and a cozy taproom where you can enjoy your beer. Find out more at the Winchester Brew Works website.

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