8 Fun & Retro Things to Do in Winchester, VA

things to do in Winchester VA

Winchester, VA, has the feel of a city that loves its modernness but still embraces its history and past. The city is filled with cool, fun places to visit and restaurants to die for. But when it comes to enjoying all of the history it has to offer where exactly do you start? From kicking it old-school movie style to skating to the oldies, here are 8 retro things to do in Winchester, VA and vicinity!

things to do in Winchester VA George Washington
Do you know what George Washington’s first local ordinance was? You’ll find out all about and how the locals honor it in Winchester!


Disclosure: I was graciously hosted by the fine folks at visit Winchester, VA, and Frederick County, Va, to give you the scoop on what to do when you’re in town. All opinions are my own!

I love exploring historical towns and cities, there’s no doubt about it. I adore the vibe, the locals, and the tried and true places that are still city hot spots. So, when Mr. Locke and I were asked to road trip to the city of Winchester, VA, there was zero hesitation to say yes.

I mean, give me farm animals and good food and I’m down! Here are our top suggestions for things to do when you’re in Winchester. 


Explore Old Town Winchester

things to do in Winchester VA Old Town Winchester
Eat, walk, and shop in Old Town Winchester. Photo Credit: Steven Locke

In the heart of Winchester is a super cool place to walk around and dine: Old Town. Completely free of cars, several blocks are brick-lined and ideal for moseying around to check out dining spots, mom and pop shops, and grab a drink if you’d like. 

Folks love to bring their dogs so, if you’re on a road trip with your furry baby, feel free to let him tag along (on a leash, of course). On select nights the city brings in local buskers to provide some live entertainment that really makes the visit super cool. 


Learn about Winchester’s Rebel Daughter, Patsy Cline

things to do in Winchester VA The Patsy Cline Experience
If you’re a Patsy Cline fan, make a pit stop at the Winchester Visitors Center and checkout The Patsy Cline Experience.

Did you know that the song “Crazy” by Patsy Cline is the #1 song on jukeboxes? I’m sure it’s up there in the karaoke scene, too. The gone-too-soon singer lived part of youthful years in Winchester and became a music scene stealer compliments of her boisterous personality and perfect-pitch voice. 

But what you may not know about the first female singer inducted into the Nashville Country Music Hall of Fame is that she was a bit too risque for many of the Winchester folks.

I learned so much about her years in Winchester on our pit stop at the Winchester Visitors Center in the “Becoming Patsy Cline” exhibit and even sat on the exact piano in one of her famous photos. 


Swoon Over Antique Cars

things to do in Winchester VA Jack's Auto Sales
Throw on your poodle skirt and saddle shoes and you’ll fit right in at Jack’s. Photo Credit: Steven Locke

If I had a choice and no budget necessary, my ideal drive would be a 1940’s truck. I’d want it to be that gorgeous shade of rusty brown but put a rust deterrent on it and give it a clear coat. Ahh, a gal can dream. 

If you love antique, restored vehicles, you’ll definitely want to head to Jack’s Auto Sales. A little bit quirky but a whole lot of fun, you can browse his latest acquisitions both indoor and out. 


Learn about the History of Shenandoah Valley 

things to do in Winchester VA Museum of the Shenandoah Valley
Beautiful crow sculptures in the outdoor garden at Museum of the Shenandoah Valley. Photo Credit: Steven Locke

Shenandoah Valley is an area that grows on me more and more with each visit. And, I have to admit, there is plenty of cool history there, especially regarding American wars. But Museum of the Shenandoah Valley is so much more.

Sure, you’ll learn about how Winchester changed hands in the Civil War 46 times (no kidding!), but there are several exhibits featuring the locals, gorgeously-pristine walking gardens, and hiking trails if you’re feeling ambitious. 


Ear Worm at Ear Food

If you know the catch phrase, “ear worm”, you know it’s a catchy piece of music that you can’t get out of your head. For 30 years, Ear Food Record Store has been selling vinyl (along with CDs and movies) to locals looking for the latest (or classic) music styles. But what I find cool is that you can find rare Patsy Cline records in the shop.


Skate to the Oldies

Since the 1950’s, Mac’s Roller Rink has been a fun spot for folks that want to work on their left turns on wheels. The roller rink plays both retro and modern songs and offers skate rentals if you don’t want to bring your own. 


Just Outside of Winchester

Only a few-minutes’ drive are these must-do retro stops:

Stephens City, VA:

things to do in Winchester VA Family Drive-In Theater
LOVE that they still use the old window speakers at Family Drive-In!

The Family Drive-In Theater  –  Sure, it plays the newest flicks on two screens, but it still offers that classic drive-in feel with metal speakers that attach to your window. Folks like to bring fold-up chairs and watch the movies al fresco and even tailgate by bringing their own meals (extra charge for tailgating). 


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