3. Bridge Cafe, 279 Water Street (1792)

Bridge Cafe

Completed in 1792, Bridge Cafe is the oldest surviving tavern and one of the oldest buildings in Manhattan. In the past, the building contained a porterhouse, a beer-serving grocer, and a brothel.

Located near the marina at 279 Water Street in the South Street Seaport area of Manhattan, the establishment attracted pirates and sailors who often hung out in the brothel drinking beer and whiskey. Besides serving great drinks, Bridge Cafe has gourmet food. In the 19th century, the building was described as a grocery, a porterhouse, or a liquor establishment and is one of New York City’s oldest historic taverns. Beware, though, if you visit this vintage bar, it may be haunted.