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10 Exciting Things to Do in Winchester, VA That You’ll Remember Forever



Winchester, VA is an absolutely stunning city in the Shenandoah Valley in the northern part of the state. It’s historically rich, culturally diverse, and wonderfully charming. To visit Winchester, VA is to visit what makes America great. There are many exciting and interesting attractions throughout the city for people from all walks of life to enjoy. Check out this list of 10 exciting things to do in Winchester, VA.

1. Begin With Old Town Winchester

An empty street in Old Town Winchester, VA.
Photo credit: Krista Trovato via Flickr

The charm of Old Town Winchester will make you feel warm and happy. The cobblestone streets and 18th and 19th Century architecture will make you feel like you’re in a simpler time. This all-American old town has been around for over 250 years and looks as though it is right out of the storybooks. Here you’ll find a variety of restaurants, museums, cafes, as well as many quaint shops. Old Town Winchester is the perfect place to soak up the classic Virginia culture.

2. Visit the Museum of the Shenandoah Valley

Photo credit: Visit Winchester VA via Flickr

The Museum of the Shenandoah Valley was formed around the massive Glen Burnie Historic House as well as the six acres of land it rests on. It opened as a museum on April 3, 2015. The museum showcases archaeological exhibits from the original inhabitants of the area, the Shawnee Natives.

The complex is split into three sections. The first is the museum itself, the second includes the beautiful gardens surrounding the house, and the third is the original Glen Burnie Historic House.

3. Take a Trip to the Shenandoah Valley Discovery Museum

The Shenandoah Valley Discovery Museum is a state-of-the-art facility that showcases hands-on exhibits designed to ignite the imagination. This museum focuses on teaching science, math, the humanities, as well as the arts to visitors of all ages. It’s the perfect place to bring your kids to learn more about what it means to be human as well as how the universe works.

4. Check Out Patsy Cline’s Adolescent Home

Photo credit: Joel Abroad via Flickr

Famous Country music star Patsy Cline lived in this house during her formative years until right before entering the music business. She lived here from 1948-1957. Today the Patsy Cline Historic House is registered on the National Register of Historic Places as well as the Virginia Landmarks Register.

Today, visitors can take tours of the house and explore the home of this legendary singer.

5. Step Foot on Stonewall Jackson’s Headquarters

Exterior of Stonewall Jackson's Headquarters in Winchester, VA. A large cannon is out front.

During the cold winter of 1861-1862, the legendary Confederate general Thomas “Stonewall” Jackson used this Hudson River Gothic Revival style house as his headquarters.

Inside you’ll find a massive collection of Stonewall Jackson artifacts. Actually, it also has the largest collection of Stonewall Jackson memorabilia. The general’s office is still the same as it was when he last used it. Therefore, you’ll truly be stepping into the past.

6. Check-in at George Washington’s Office

Exterior of George Washington's Office Museum in Winchester, VA.

From September 1755 to December of 1756, General George Washington used this little house as his office while planning and overseeing the construction of Fort Loudon.

The museum exhibits a variety of artifacts including a large cannon, surveying equipment, as well as a scale model of the town of Winchester built in 1755. On the north end of the model is Fort Loudon.

7. Explore the Shenandoah Valley Civil War Museum

In front of the Shenandoah Valley Civil War Museum in Winchester, VA.

Over 3,000 Civil War artifacts are showcased here at the Shenandoah Valley Civil War Museum. The building itself has graffiti from both Union and Confederate soldiers because it was used by both at different times. This Georgian style courthouse was used as a hospital, an army barracks, as well as a prison by both Union and Confederate soldiers during the Civil War.

8. Get Lost in the Handley Regional Library

The Handley Regional Library in Winchester, VA.
Photo credit: Brent Moore via Flickr

The Handley Regional Library is a recent contribution (in comparison to the rest of the buildings) to the city of Winchester, VA. Judge John Handley set aside $250,000 dollars in his will to erect a public library for the residents of Winchester. What makes it special, besides the beautiful architecture, is that it is free to use forever.

9. Stroll Through the Mount Hebron Cemetery

Outside at the Mount Hebron Cemetery in Winchester, VA.
Photo credit: Visit Winchester VA via Flickr

One common enclosure connects the four different burial grounds at Mount Hebron Cemetery. This 5-acre cemetery was created after the combination of the old Reformed and Lutheran cemeteries that make up the burial grounds. The cemetery was opened to much fanfare and excitement and today it serves as a beautiful communal place to honor the ancestors of Winchester, VA.

10. Step Back in Time at the Fort Loudoun Historic Site

The entrance sign to the Fort Loudoun Historic Site in Winchester, VA.

Last, but definitely not least, is the Fort Loudoun Historic Site. This is a very important historic place that served as General George Washington’s headquarters during the French and Indian War.

Today, the only pieces of the original Fort Loudoun include the well as well as some remnants of the bastion. Many artifacts were discovered on the underneath the barrack’s foundation. This historically important location now has a house (built in the 1850s) on the property, will soon serve as an interpretive center for visitors.

What Are You Waiting For? See Winchester, VA for Yourself!

The history of Winchester, VA is long and complicated. It is also home to many important historical events. Today, it stands as a beacon of true Americana and as a representation of small-town charm. So, the next time you’re in the state, you should strongly consider doing yourself a favor and visit Winchester, VA.

John Ghost is a professional writer and SEO director. He graduated from Arizona State University with a BA in English (Writing, Rhetorics, and Literacies). As he prepares for graduate school to become an English professor, he writes weird fiction, plays his guitars, and enjoys spending time with his wife and daughters. He lives in the Valley of the Sun.