Old Homestead > Location:New York City, New York > Year opened:1868 The oldest continuously operating steakhouse in America, and arguably the oldest restaurant in New York City, the Old Homestead was originally a tiny restaurant, operated by the Heinz family as part of the Tidewater Trading Post, serving what was then the waterfront (the Hudson River once reached nearly to its doors). The place expanded as the river receded, growing into a full-scale steakhouse, and in the 1940s, it was bought by a longtime employee, Harry Sherry. His grandsons own and operate it today.
Fraunces Tavern in NYC may not be the oldest, but still a great place where George Washington gave his retirement speech to his officers. Also in Miami Florida, Tobacco Road. The oldest bar in Miami. It had hidden stairways in the back during the speakeasy days. Jazz upstairs and Blues downstairs. Liquor license 001 in Dade County. Two of my favorites for what it’s worth.