Nightlife
Nightlife
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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.
- 3111 Valley Ave.
Winchester, VA 22601 - (540) 667-9995
- ijcanns.com
- 3111 Valley Ave.
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James Charles Winery
Located only 5 miles from Old Town Winchester, this winery offers tastings, tours, live entertainment on weekends, and special events.
- 4063 Middle Road
Winchester, VA 22602 - (540) 931-4386
- jamescharleswine.com
- 4063 Middle Road
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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.
- 107 West Boscawen Street
Winchester, VA 22601 - (540) 665-9437
- facebook.com/MilanosRistoranteAndBar
- 107 West Boscawen Street
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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.
- 125 East Piccadilly Street
Winchester, VA 22601 - (540) 535-1899
- piccadillypublichouse.com
- 125 East Piccadilly Street
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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.
- 120 Indian Alley N, Suite 100
Winchester, VA 22601 - (540) 686-0545
- www.taylorwineroom.com
- 120 Indian Alley N, Suite 100
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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.
- 101 North Loudoun Street
Winchester, VA 22601 - (540) 722-2055
- theunionjackpub.com
- 101 North Loudoun Street
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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.
- 1687 Marlboro Road
Stephens City, VA 22655 - (540) 869-9567
- valeriehillwinery.com
- 1687 Marlboro Road
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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.
- 7783 Main Street
Middletown, VA 22645 - (540) 869-1797
- www.thewaysideinn1797.com
- 7783 Main Street
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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.
- 320 N. Cameron Street
Winchester, VA 22601 - (540) 692-9242
- winchesterbrewworks.com
- 320 N. Cameron Street