2. Mount Pitt
View of the city and harbor of New York, taken from Mount Pitt, the seat of John R. Livingston. Photo from NYPL.
Also known as Ranelagh, Mount Pitt was one of the highest natural points on Manhattan island. This 60-foot hill had views of lower Manhattan and the East River that residents today would fight for. Speaking of fighting, Mount Pitt was home to Fort Pitt during the Revolutionary War, though the fort was dismantled soon after. Eventually, Mount Pitt itself was leveled to make room for Pitt and Grand Streets. It goes without saying, the view isn’t quite the same today.