Old Town Winchester: shopping and history


Hessians who came to fight against American independence came to Winchester and decided to stay. They built sturdy stone structures like this one in Old Town.

Petula Clark once sang a song praised the sights and sounds of Downtown. “Things will be great when you’re downtown.”

I’m dating myself but I was a really little kid and didn’t know much beyond my backyard when that song played on the radio.

But it made an impression. I have always loved Downtown. No matter what Downtown it is…Baltimore, Annapolis, Carlisle, Pa., or Winchester, Virginia.

A recent trip took me to pretty, historic Winchester, a pre-Civil War town tucked in the Shenandoah Mountains. Washington really did sleep here. And work here. And get his first taste of politics here. A member of the House of Burgesses, he worked on a law to ban pigs from running through the streets of Winchester. Even great people have to start somewhere.


This little guy, who hangs out near Washington’s office, is a reminder of Washington’s first piece of legislation.

I saw no pigs but found a friendly little downtown with cool shops, a couple of restaurants worth trying, a children’s museum and a library that shouldn’t be missed.

The downtown area, a walking mall,  is pedestrian friendly — cars can cross only at one intersection. So on a pretty afternoon, the place was crawling with moms and their children, couples window shopping, and friends enjoying a meal al fresco.

The Shenandoah Valley Civil War Museum is housed in the


Find a new love at the Winchester Book Gallery.

original 1840 courthouse. The Shenandoah Valley Discovery Museum, at the end of the district in a former furniture store, has several floors of fun for children. The Handley Library is really around the corner — but you have to stop in to see the beautiful dome and the glass floor.

We wandered through all kinds of shops. We found books, gourmet snacks, earrings,


Small town shopping is filled with treasures like this.

doodads and thingamajigs. You know… the kind of merchandise you want to buy for yourselves and all your loved ones.

Don’t miss the history along the way including the Taylor Hotel once used as a Confederate hospital and George Washington’s little office (now a museum).

If you get hungry, you have your choice of eateries. We enjoyed the Union Jack Pub, and Roma Pizzeria but there were plenty of other good spots for breakfast, lunch and dinner along the way.


The Handley Library isn’t on the pedestrian mall but it’s worth a detour.

This is one of those places where Petula was right. “You can forget all your troubles, forget all your cares….”

Ⓒ Text and photos Mary K. Tilghman


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