I thought this Britannica map of the New York Harbor area in 1885 was pretty interesting. It shows how the West Bronx had been incorporated into the city long before Brooklyn, Queens, Staten Island, or the East Bronx would be — and why the remaining detached Victorian houses in that area are significant to New York City‘s urban history, as opposed to the separate histories of Brooklyn or Flushing or other towns that were unfolding during the same time period. Mainly because of its shape, the map also gives a good look at where the larger cities in North Jersey were at the same time.
I like the inebriate and lunatic asylums on Ward’s Island. And also the way that the cartographer jumped the gun on the first Hudson Tube (showing a “Tunnel” between Greenwich Village and Jersey City). That’s not entirely wrong — it actually was been being attempted in 1885, and the mapmaker probably didn’t want to leave off an important project. But due to legal, financial, and engineering challenges, it wouldn’t be finished until 22 years later, in 1907.
Update: I found a companion plate that shows the details of Manhattan below Central Park. It includes the names of the ship lines on the Hudson River and East River piers, and Thirteenth Avenue.