Nightlife
Nightlife
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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.
- 103 E. Piccadilly Street
Winchester, VA 22601 - (540) 678-4700
- georgesfoodandspirits.com
- 103 E. Piccadilly Street
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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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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.
- 7843 Main Street
Middletown, VA 22645 - (540) 868-9877
- facebook.com/nanasirishpubmiddletown
- 7843 Main 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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Sweet NOLA’s
Sweet NOLA’s Southern Food Lounge is a celebration of southern and New Orleans food, lifestyles, and music.
- 688 North Loudoun Street
Winchester, VA 22601 - (540) 667-6652
- sweetnolas.com
- 688 North Loudoun Street
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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 226045 - (540) 869-1797
- alongthewayside.com
- 7783 Main Street