• Umberto’s Pizza and Pasta

    Neighborhood Italian restaurant offering signature subs, gourmet pizzas, pasta, and Italian specialties.

  • 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.

  • 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

    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.

    Wayside Inn
  • 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.