gold cup wine bar

Enjoying a sophisticated ambiance and fabulous setting, Gold Cup Wine Bar is a relaxing venue for cocktails and delicious fare. Serving lunch and dinner, Gold Cup offers delectable menu options, the best of Virginia’s wines, signature cocktails and much more. Our sushi menu is available Wednesday - Sunday. Dogs are welcome on our outdoor terrace daily.

Hours: Open Daily 11:00 a.m. - 12:00 a.m.

Seating is on a first-come, first-serve basis. For additional information, please call 540.326.4070.

weekly specials

5:00 p.m. - 8:00 p.m.

Mondays - $6 burgers, $5 drafts, $5 rail cocktails

Tuesdays - 1/2 priced appetizers, 1/2 priced bottles of wine

Winery of the month

Join us every Sunday 2:00 p.m. - 4:00 p.m. for complimentary tastings from our Winery of the Month.

October: Sunset Hills Winery
November: Narmarda Winery
December: Creek’s Edge Winery


Sunday Funday has been redefined with our weekly event! From 4:00 p.m. - 7:00 p.m., enjoy our sensational views, feast on our fresh al fresco menu, spoil yourself with our seasonal beverages and take in the sounds of an acoustic guitar all while enjoying the summer sun on our terrace. Performances include hometown artists to professional recording artists from Nashville, TN. 


Our dog-friendly event returns May 15! Join us every Tuesday from 5:00 p.m. - 7:00 p.m. to treat your dog and yourself to Yappy Hour! Watch as your pooch tests their skills in the obstacle course while you indulge in the special ‘Sharable Chow’ menu including Dog Collars (housemade onion rings with truffle aioli) and refreshing Pup-tail Menu with our Spicy Pup-arita with Blanco tequila. A portion of the proceeds are donated to the Middleburg Humane Foundation.