5. Queensboro Bridge (Blackwell’s Island Bridge)

Photo from Library of Congress circa 1908

The Queensboro Bridge initially helped transform Queens from rural to urban borough. The bridge is also featured on the path taken by F. Scott Fitzgerald’s wealthy characters in The Great Gatsby, traveling from Long Island to Manhattan. There was once a trolley that ran across, with a stop mid-span. A staircase brought riders down to Roosevelt Island.