• 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
  • 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
  • The Wine Room at Taylor Pavilion

    This urban wine bar with an industrial chic interior and modern vibe, features over 100 international wines by the glass and bottle, a creative culinary menu, and Sunday Brunch.

  • 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
  • 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
  • Winchester Brew Works

    This lively nano-brewery steps from the Old Town Walking Mall offering 9 rotating taps. Special events include team trivia, food trucks, music, and more.

    Winchester Brew Works