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14 Travel Photos to Inspire a Weekend Trip to Winchester, Virginia

Browse through a collection of my favorite photos captured in Winchester - and see if these inspire you to visit the Virginia city.

By Jason Barnette | Travel writer and photographer with 15+ years of road tripping experience

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I had just finished three days in Shenandoah National Park when I rolled into Winchester, Virginia. It was an unusually hot and humid weekend in late summer – complete with epic thunderstorms and torrential downpours. But the clouds parted, and I found myself exploring one of the most gorgeous downtown areas I’ve come across in a small town.

I was too excited to capture photos throughout downtown, inside the museums, and everywhere I explored in Winchester. The old world charm added a layer of tranquility to the experience. Here are a few of my favorite photos from the visit.

Located beside the visitor center, Abram’s Delight was a great place to begin my exploration of Winchester. Through a guided tour of the historic home I learned about the early history of the frontier town and picked up more than a few tips for the visit.

Stonewall Jackson’s Headquarter was another fascinating house museum in Winchester, but I wasn’t allowed to capture any photos inside. Instead, I made do with this photo of a canon on display in the front yard.

The biggest reason I wanted to spend a couple of days in Winchester was the town’s connection to George Washington. At just 16 years old, Washington worked as a frontier land surveyor for a proprietor. This statue of Washington is probably the only one to depict him as a teenager.

Admittedly, the Patsy Cline Historic House wasn’t much to photograph. It was a very simple home – kept much the way as when she lived there. But I laughed when I captured this moment because just a week earlier I had told someone a museum isn’t complete with a Singer sewing machine.

The most surprising thing I discovered in Winchester was Old Town. The center two blocks of town are devoid of traffic, instead allowing pedestrians only to walk the brick street connecting shops, restaurants, and homes.

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Old Town was simply gorgeous and one of my favorite photographic subjects of the year. Restaurants featured outdoor seating, gardens were planted in the shade of trees, and historic stone buildings stood between modern structures.


When a summer thunderstorm hits, the best thing to do is head indoors. After a short drive, I found myself in the giant barn at Marker-Miller Orchards Farm Market. Bins of freshly picked apples – it was early September – were stacked around jars of apple butter and jam.

The Shenandoah Valley Civil War Museum was located inside an old courthouse in Old Town. The original courtroom was one of the most gorgeous I’d ever seen with white walls and daylight flooding inside from large windows. The small museum had a collection of artifacts – including old rifles on display.


I have always been a fan of exploring cemeteries and Mount Hebron Cemetery was no exception. The grand entrance through a castle-like office building led to a stunning cemetery around large oak trees. It was practically a work of art and the last place I explored in Winchester before leaving town on U.S. Highway 50.

2 Responses

    1. I really, really loved Winchester. I want to go back. Be sure to come back to the website tomorrow – I’m getting ready to post a road trip itinerary that starts in Winchester!

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Do you have a question about travel or road trips? Are you a CVB or DMO interested in working with me? I typically respond to emails within 24 hours. Quicker if you include a good riddle.
Do you have a question about travel or road trips? Are you a CVB or DMO interested in working with me? I typically respond to emails within 24 hours. Quicker if you include a good riddle.

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