One of the oldest drinking establishments in New York, this federal–style townhouse was originally home to James Brown, an African aide to George Washington during the Revolutionary War. If you look closely at the famous painting of Washington crossing the Delaware, you can see Brown sweep-rowing in the skiff’s bow. By the mid-1800s, it was being operated as a pub, as it continues to be to this day. The nautical trappings—including the cleats by the front door—aren’t just a gimmick. They’re reminders of a time before the Hudson River had been filled in to West Street, and the water came within five feet of the Ear Inn’s front door. If you’re looking to get soused yourself, this is the place to do it. Just make sure you have something to eat, too—the food is better than you’d expect. —Nathan King

Nathan King is a Deputy Editor at AIR MAIL