Arguably America’s oldest restaurant is the Union Oyster House, and given that the famous and the familiar have frequented this iconic landmark since 1826, few secrets exist about the place. But one little-known fun fact is that future French King Louis Phillipe taught French classes on the 2nd floor while living here in exile from 1796-1797. Booth number 18 is very popular because it is where John F. Kennedy would often come for lunch. (Warning: It is often booked well in advance, but plan to eat here during off-hours and you may find yourself dining in JFK’s booth.) For a genuine neighborhood feeling, join the locals at the downstairs oyster bar to slurp up the beautiful bivalves over a cold beer and small talk.

41 Union St.