Jockey Hollow Bar + Kitchen

Four concepts inside the restored Vail Mansion.

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Jockey Hollow occupies the 1916 Vail Mansion at the top of South Street and splits the building across four concepts: the formal main dining room downstairs, the upstairs Vail Bar, an Oyster Bar with a marble counter, and a set of private dining rooms used for events.

Restaurateur Chris Cannon’s flagship since the building was restored, it’s the dressier choice when an evening calls for occasion dining. Closed Sunday and Monday; reservations recommended on weekends.