Atmosphere and menu pair together well in Winchester, Va.
October 2026
by Peggy Hyland, Contributing Columnist
On Winchester’s charming downtown pedestrian mall, Water Street Kitchen is serving up classic comfort food in a relaxed atmosphere. It is located in one of the fixtures of the Old Town historic district, where Boyd’s Drug Store stood for about a century.
There are traces of the old drug store and soda fountain still present, from the tin ceiling to the ornate shelving that lines the walls. Even the name is a nod to the past, when South Loudoun Street was known as Water Street. We soaked in the feeling of familiar warmth and nostalgia from the moment we stepped inside. The vintage atmosphere felt timeless, not dated. Service was friendly and helpful, especially when perusing the side dishes.
The selection of side dishes was extensive, but there was no need to pick just one. The Side Plate meal option features three sides and a piece of corn bread, perfect for sharing with friends during an afternoon of shopping and strolling. I could eat the Cajun fried okra all day long. We also tried the mac and cheese, a delectable dish with cavatappi noodles bathed in rich, creamy cheese.
Crab dip always catches my eye, and this dish was fabulous. It was a creamy indulgence, with generous chunks of crab meat. The pimento cheese gave it a homey, southern feel, and the crumbled bacon topping added some crunch to the texture.
My companion chose the meatloaf, made with Black Angus beef and prepared in the classic style. The house-made gravy will bring back memories of visiting a favorite grandmother for a Sunday meal. He chose the freshly cooked kettle chips, a crunchy delight, and the crispy Brussels sprouts, cooked just right. I could not resist the shrimp and grits, which was truly outstanding. The stone-ground grits had the perfect texture, and the mild cheddar added rich velvetiness. The sauce of fire-roasted tomatoes, peppers and onions was terrific on its own, but paired with the blackened shrimp and luscious grits, the combination was a dream team. The grits are also available as a side dish.
With breakfast served all day, Water Street Kitchen is a great place to start — or end — your day of exploring all the shops and historic sites on the Loudoun Street Pedestrian Mall. It’s right around the corner from Taylor Pavilion, where a variety of free events are held throughout the year, and a half a mile from the home of Winchester’s famous star, Patsy Cline.
Water Street Kitchen
2 S. Loudoun St., Winchester, VA 22601
Monday through Friday, 11 a.m.-8 p.m.; Saturday, 10 a.m.-8 p.m.; Sunday, 10 a.m.-3 p.m.
540-313-4680
Waterstkitchen.com