Casual and Fine Dining
Casual and Fine Dining
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Umberto’s Pizza and Pasta
Neighborhood Italian restaurant offering signature subs, gourmet pizzas, pasta, and Italian specialties.
- 170 Delco Plaza
Winchester, VA 22602 - (540) 722-3811
- www.umbertoscatering.com
- 170 Delco Plaza
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Union Jack Pub & Restaurant
Located in the Historic Union Bank Building, Union Jack serves quality classic British and American fare. Their 50-foot British inspired bar offers 38 rotating drafts on tap, & a huge selection of European, Craft beers, & wines.
- 101 North Loudoun Street
Winchester, VA 22601 - (540) 722-2055
- theunionjackpub.com
- 101 North Loudoun Street
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Up in Smoke BBQ
Up in Smoke serves traditional favorites cooked the old fashioned way, low and slow. Pulled pork, Texas style brisket, along with more modern offerings like Korean BBQ tacos, Tex-Mex brisket tacos, spicy baked beans, and light and fresh coleslaw.
- 692 N. Loudoun Street
Winchester, VA 22601 - (540) 327-7619
- www.upinsmokebbqandcatering.com
- 692 N. Loudoun Street
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Village Square Restaurant
New American fine dining served in the casual atmosphere of a historic building in Old Town Winchester.
- 103 N. Loudoun Street
Winchester, VA 22601 - (540) 667-8961
- www.villagesquarerestaurant.com
- 103 N. Loudoun Street
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Violino Ristorante Italiano
This family owned restaurant with cozy indoor seating and seasonal patio dining serves authentic Northern Italian cuisine using fresh, local ingredients.
- 181 N. Loudoun Street
Winchester, VA 22601 - (540) 667-8006
- violinoristorante.com
- 181 N. Loudoun Street
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Water Street Kitchen
Water Street Kitchen offers down home cooking with a new take on classic Americana cuisine, utilizing locally sourced ingredients.
- 2 S. Loudoun Street
Winchester, VA 22601 - (540) 313-4680
- waterstkitchen.com
- 2 S. Loudoun Street
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Wayside Inn
A truly unique experience, Wayside is said to be the oldest and longest running inn in the United States. Situated in the quaint town of Middletown, Wayside offers lodging, dining, and entertainment.
- 7783 Main Street
Middletown, VA 226045 - (540) 869-1797
- alongthewayside.com
- 7783 Main Street
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West Oaks Farm Market
The deli and market café at West Oaks serves breakfast, lunch, and dinner, and features deli sandwiches, made-to-order burgers, soups, salads, appetizers, and desserts.
- 4305 Middle Road
Winchester, VA 22602 - (540) 539-8175
- www.westoaksfarm-market.com
- 4305 Middle Road
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WincFood
Winchester offers over 200 restaurants! This useful directory has reviews, special deals, and listings for all restaurants within the city limits.