5. King’s Bridge

According to Untapped Cities’ History Editor, Benjamin Waldman, the original King’s Bridge (and New York City’s first) seems to have been built in 1693 and then rebuilt in 1713. The History of the City of New York hints at a bridge going over a canal that could be it:

The ” Brugh straat,” or Bridge street, still retains its name; the circumstance from which it was derived being, that it led to the bridge crossing the ditch at Broad street.

Here’s a second instance:

… we shall cross the bridge over the canal, running up Broad street, and continue our description of what was then called ” The Water,” and sometimes ” the Water-side,” designated at present as the north side of Pearl street, between Broad and Whitehall streets, the history of which is as follows : The first church built in this city was erected in 1633, on the present north line of Pearl street, about the middle of the block between Broadway and Whitehall street. This church presented its prominent front to the waiter; but the entrance was mainly from the rear, at the present Bridge street, which was then a wagon road, leading to the bridge across the ditch at Broad street.

Today, the High Bridge is New York City’s oldest bridge, but history buffs like to point out a technicality: the King’s Bridge is still rumored to exist — just underground.