Just over the Clarke County line is the historic and culture-rich city of Winchester, VA. Founded in 1752, the architecture and shops are as diverse as the people, which has attracted an exceptional mixture of restaurants, big and small. Here are our top five picks from around the city.

Picadilly’s Public House & Restaurant | 125 E Piccadilly Street

Built in 1900 as a grocery warehouse, Piccadilly’s has been restored to its roots in feeding the public. The original brick walls, refurbished floors, ceilings and windows transport you back to a simpler time – a time when quality of product and service was key. Today’s staff of Piccadilly’s are no different, putting flavor and service above all else.

Smokey T’s Southern Kitchen* | 1488 Senseny Road

Smokey T’s is as much about the preservation of local history as it is the meats it serves on smokehouse style sandwiches, meat in three style dinners (including a catfish sandwich – pictured above – that is out-of-this-world) and families gathering over a shared meal while listening to live music. Chef Becky Tomlin uses time tested curing, brining and smoking techniques on Smokey T’s signature meats. The selection of craft beer is the stuff of any home-brewers dreams with 12 rotating taps and over 500 bottles/cans that can be enjoyed on site or bought to take home.

*Now closed

The Butcher Station | 3107 Valley Avenue #106

“Fresh food tastes better. Local food is fresh; therefore, local food tastes better.” That’s the philosophy of The Butcher Station, and it shows. From the restaurant to the market, they use locally-sourced ingredients wherever and whenever possible. The result is a local favorite sure to be at the top of your list.

Neighborhood Italian Kitchen | 1202 Berryville Avenue

With over 400 5-star reviews on Trip Advisor, we would be remiss not to include this place on our Guide. If you’re looking for an authentic Italian experience like you’d have in New York, you won’t be disappointed. From pizza to pasta to homemade mozzarella crafted on site, NIK is definitely worth a stop.

Hopscotch Coffee & Records | 250 Millwood Avenue

For true-blue coffee lovers and vinyl album enthusiasts, Hopscotch Coffee & Records is an experience. After you order you’re top-notch beverage, you can enjoy the intimate coffee bar or the expansive 2-story back area with vinyls on display and for sale.


More links for your trip to Winchester:

Learn All About the City of Winchester

Fun Family Events in Old Town

The 15 Best Things to Do in Winchester

This content is not the product of the National Association of REALTORS®, and may not reflect NAR's viewpoint or position on these topics and NAR does not verify the accuracy of the content.