Across from the Shenandoah Valley Civil War Museum (which served as a prison during the War and the old Winchester Courthouse) is another semi-historic venue. But this one you can eat in.
Union Jack Pub & Restaurant has restored the old Union Bank building in Old Town Winchester (North Loudon Street) to its original 1878 appearance to provide tourists and locals with a unique dining experience. The aesthetic of the place reminds one of an English pub, and that was completely intentional. As the name suggests, the menu is packed with Brit-inspired dishes and some recognizably American pub faire. Their lunch menu is loaded with sandwiches, salads, and burgers served throughout the day to fit the appetite of any walk-in guest or family. Appetizers are standard, including spinach and artichoke dip, hummus, wings, jumbo pretzels, loaded chips (fries), and sliders. Their selection of burgers and sandwiches are also familiar, but with British-themed names like the Pub Burger, Union Jack Dip, and Jack’s Burger. However, they include a few wildcards that some Yankee diners may find enticing, like the Yorkshire Pudding, Tikka Masala (an Indian spiced curry entrée), Union Jack’s Fish & Chips, Bangers and Mash, and a Steak & Gorgonzola Salad. The restaurant, like many in Old Town Winchester, offer outdoor seating as well as an upstairs lounge for their Happy Hour specials, providing a great view onto Loudon Street. The main indoor dining room is separate from the bar, both with their own unique décor and aesthetic.
Now, before you start to think that this place is just like “any other pub-style restaurant” I encourage you to think again. The theme and interesting menu selections set Union Jack apart from the other pubs. This isn’t an Applebee’s knock-off by any means. The atmosphere and the food make this a dining spot worth visiting, whether for a quick bite or a pint.
We took our pitstop at Union Jack during our first visit to Winchester after taking the Old Town Winchester Civil War Walking Tour (which you can collect a brochure for at the Winchester Visitor Center or download online). We had done a fair bit of walking that morning and I relished a break from the heat inside a cool, air conditioned restaurant. Union Jack hit the spot, both in temperature and in food. Their Bourbon BBQ Bacon Burger was just the right balance of tangy and satisfying without being overly messy or drippy – something I hate in BBQ sandwiches, but I wanted to be adventurous that day. Their chips (fries) were thick and looked to be hand-cut, something I miss from childhood years. It was entertaining to sit and gaze at the British-themed décor while we ate, giving us a short intermission from the heavy Civil War exploring we had been doing all day.
Overall, a great respite during any history trip. North Loudon Street (and pretty much all of Old Town Winchester) is open to pedestrians only. This means you’ll need to park elsewhere. I recommend Old Town Parking Garage at 30 N Braddock St, Winchester, VA 22601. Below are links to the Civil War and the Old Town History & Architecture Tour brochures as well, for those interested.
Hours: Tues, Wed & Fri: 3pm-7pm
Address: 101 North Loudoun Street, Winchester, VA 22601
Old Town Winchester Civil War Self-Guided Tour: https://visitwinchesterva.com/wp-content/uploads/2009/04/CivilWarWalkingTour.pdf
Old Town Winchester History & Architecture Self-Guided Tour: https://visitwinchesterva.com/wp-content/uploads/2018/06/HistoryandArchitectureBrochure_web.pdf