One if by Land, Two if by Sea

Set in an 18th-century carriage house long associated with Aaron Burr, One if by Land has been New York's shorthand for a proposal dinner for decades. The formula is unapologetic: a brick-walled dining room, a working fireplace, fresh flowers, a pianist, and beef Wellington as the signature. It could feel like a museum piece; instead it feels like a room that knows exactly what job it has and does it with a straight face.

People roll their eyes at the reputation right up until they are sitting in the candlelight, at which point most of them stop. If you have one genuinely momentous dinner to book in Manhattan — an engagement, a milestone anniversary — this is the room built for it.