Amy's Creative Pursuits: Old Town Winchester West Virginia

Wednesday, May 6, 2026

Old Town Winchester West Virginia

This is part three of a travel series to West Virginia. To start at the beginning, go HERE!

After hiking the Maryland Heights Trail at Harpers Ferry we were exhausted, so spending 45 minutes in the car on the way to the town of Winchester where we would spend the night, felt wonderful.

After the refreshing car drive, we checked into our hotel then headed for Old Town Winchester where we would grab some dinner.

Old Town Winchester is a 250 year old marketplace, and my favorite part is it's pedestrian only! I love it when I don't have to deal with traffic on a town's Main Street, plus I get great photos of the old buildings.

Old Town Winchester is located within the heart of a 45-block National Register Historic District and is bursting with outdoor cafes, fun & specialty retail shops, historic attractions and family-oriented activities throughout the year.

The Loudoun Street Pedestrian Mall has earned a listing on the National Register of Historic Places Travel Itinerary.

This post will be heavy-laden with photos of these old buildings because I just loved them all. Everywhere I looked was a feast for the eyes.

We chose to eat at Roma's Old Town Wood-Fired Pizzeria and it was delicious! Somehow I forget to take a photo of the pizza; that almost never happens. We must have been hungry. 😋

This is the Shenandoah Valley Civil War Museum which sadly we didn't get to visit because it was closed. The museum is housed in the historic Fredric County Courthouse. It was built in 1840 and used as a hospital, prison, and barracks during the Civil War.

I just loved the brick roads!

The Winchester Masonic Lodge 😟

The Taylor Hotel has a rich history of travelers and Civil War stories to tell.

The varied styles of buildings in Old Town Winchester was so interesting, This building looks more like an old house than a store front.

And look at that little grill building sandwiched between two tall buildings.

Quite the Post Office isn't it?

This beauty was a woman's clothing shop (men's clothes were a separate business in the basement). I actually went inside this one, mostly because I wanted to see the interior of the building and it did not disappoint. I just love shopping in old historic buildings; although I must admit I tend to be more interested in the buildings than the items for sale in the buildings 😊

And would you believe this is their public library? In all my life I have never seen a more extravagant public library, and it was built in 1913 to be the citie's library. It wasn't like it was built for another purpose and then repurposed into a library. I find it so fascinating that they would built such an amazing building for a library.

Thank goodness it was open and we could check it out. There was a book in the foyer that explained all about the libraries origins. Just look at that photo with the horse and carriage, wouldn't you just love to step back into that time period?

The dome was just gorgeous. The design of the library was to resemble an open book with the dome representing the spine and the wings representing the covers. I don't really see it, but hey, it's beautiful nevertheless.

Just look at these curved staircases! Be still my heart!

Of course we had to climb those stairs!

The view from the second balcony.

They even had a spiral staircase!

After our library tour, we headed back to in the direction of our parked car as it was getting late. This place looked interesting, but they were closing up as we were walking by.

I continued to "ooh" and "ahh" over the architecture; it reminded me a lot of Savannah Georgia.

As I walked these historic streets it made me wonder about all the people who lived here and life way back then.

There was such a variety of buildings from brick, to stone, to wood...all unique and different. Usually when you visit a historic town all the buildings seem similar, but not here.

I wish Old Town Winchester wasn't so far away. I'd love to come back someday when the pedestrian mall was hustling and bustling. But I doubt I'll ever get here again as there is so much else to see in the world and I don't have a lot of time left at 63 years old.