• 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.

  • Uno Pizzeria / Half Note Lounge

    Located in the award-winning George Washington Hotel, Uno Pizzeria & Grill serves classic breakfast favorites and American fare at dinner. Enjoy both indoor and outdoor seating, a casual bar, and great happy hour specials.

    George's Food and Spirits

  • Valerie Hill Vineyard and Winery

    Valerie Hill’s Tasting House is a Federal style brick manor home built in 1807. Open daily year-round, visitors can enjoy wine tastings, light fare, live music, and special events.

    Valerie Hill Vineyard & Winery

  • Vault and Cellar

    Serving elegant Appalachian style cuisine, Vault and Cellar is located in a historic bank building and also offers an extensive bar menu and bourbon flights.

  • Village Square Restaurant

    New American fine dining served in the casual atmosphere of a historic building in Old Town Winchester.

  • Violino Ristorante Italiano

    This family owned restaurant with cozy indoor seating and seasonal patio dining serves authentic Northern Italian cuisine using fresh, local ingredients.

  • Water Street Kitchen

    Water Street Kitchen offers down home cooking with a new take on classic Americana cuisine, utilizing locally sourced ingredients.

  • Wayside Inn & Larrick’s Tavern

    Since 1797, a truly unique experience, situated in the town of Middletown, Wayside offers dining, lodging, and entertainment. Menu offers casual-upscale and seasonal items for your dining pleasure. Dinner & breakfast offered, visit website for hours.

  • 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.

  • WincFood

    Winchester offers over 200 restaurants! This useful directory has reviews, special deals, and listings for all restaurants within the city limits.

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