• George’s Food and Spirits / Half Note Lounge

    Located in the award-winning George Washington Hotel, George’s Food and Spirits and offers casual dining and American cuisine. Visit the Half Note Lounge for light fare and cocktails. Live music on weekends.

    George's Food and Spirits
  • IJ Canns American Grille

    Serving fine American cuisine, IJ Canns offers a full bar, outdoor seating, and Sunday brunch. The lounge offers weekend comedy and live music.

    IJ Canns Winchester
  • Milano’s Ristorante and Bar

    Milano’s serves traditional American and Italian fare, and is known for a lively bar scene with DJs and dancing. Great place to watch the big game.

    Milano's Ristorante and Bar
  • Nana’s Irish Pub

    Family-owned restaurant and pub serving traditional Irish dishes along with the finest Irish whiskeys and beers. Live music, outdoor seating, and quiz nights.

    Nana's Irish Pub
  • Piccadilly’s Public House

    Restaurant and pub serving traditional American cuisine. Piccadilly’s hosts live entertainment on weekends, and has a large outdoor patio with stage.

    Piccadillys Public House
  • Sweet NOLA’s

    Sweet NOLA’s Southern Food Lounge is a celebration of southern and New Orleans food, lifestyles, and music.

    Sweet NOLAs
  • Thai Winchester I

    Full service restaurant with patio seating and full bar featuring authentic Thai cuisine and drinks. Carryout and delivery available. Two locations.

  • Thai Winchester II

    Full service restaurant featuring authentic Thai cuisine and drinks. Visit their second location on the Loudoun Street Mall.

  • 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.

  • 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