• 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
  • James Charles Winery

    Located only 5 miles from Old Town Winchester, this winery offers tastings, tours, live entertainment on weekends, and special events.

    James Charles Winery
  • 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
  • Stephens Jazz Café

    This historic Jazz cafe serves American cuisine and a slice of history at its location next door to the home of the late local Jazz great John Kirby. Live entertainment.

    Stephen's Jazz Cafe
  • Sweet NOLA’s

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

    Sweet NOLAs
  • 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.

  • 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