Opened in 1842, High Bridge is New York City's oldest surviving bridge. The original stone arch bridge was designed to carry fresh water, via the Croton Aqueduct, without impeding shipping traffic on the Harlem River below. In 1864, a pedestrian walkway was added to the bridge. In 1929, five of the masonry arches above the river were replaced with a single steel arch, simplifying navigation. The bridge continued to carry Manhattan-bound drinking water until 1949.

The Robert F. Kennedy Bridge (formerly the Triborough Bridge) is actually three bridges, a viaduct, and 14 miles of approach roads connecting Manhattan, Queens, and the Bronx. Construction began on the bridge in 1929, actually on the day of the stock market crash, October 25th. The construction barely continued after early 1930 due to extreme financial instability. The project was "saved" by Robert Moses in 1932-1933 when he advocated the the state legislature to create the Triborough Bridge Authority to fund, build, and operate the Bridge. He unsurprisingly became the head of the Authority. The bridge officially opened to much fanfare on July 11, 1936.

When the George Washington Bridge opened in 1931, it was the longest single bridge span in the world. 19 days before this photo was taken, it lost that title to San Francisco’s brand-new Golden Gate Bridge.

Completed after 13 years of construction, $15 million, and the death of one engineer and the debilitation of another, the Brooklyn Bridge was the largest suspension bridge in the world (until 1903 when 4.5 more feet gave the Williamsburg Bridge the title)

The Manhattan Bridge was the final suspension bridge constructed over the East River. The bridge opened in 1909. The design of the bridge was especially innovative and it served as a model for many subsequent suspension bridge. The original Brooklyn approach to the Manhattan Bridge included two massive sculptures designed by Daniel Chester French. The 12 foot tall female figures symbolized the supposed attributes of the boroughs the bridge touched. Manhattan is prideful and powerful over money and world affairs, while Brooklyn is more artistic and education focused.

The Williamsburg Bridge was the second suspension bridge over the East River, completed in 1903. It was the longest suspension bridge in the world until 1924. Decades of neglect left the bridge dangerous unsafe, and it was substantially repaired throughout the 1990s and 2000s.

In the foreground, pedestrians walk on the 155th Street Viaduct, over Coogan’s Hollow. In the background are the two spans of the Macombs Dam Bridge, opened in 1895: first, a swing bridge over the Harlem River; second a camelback span over railroad tracks on the Bronx side.

The old Meeker Avenue Bridge is here photographed 10 days before its closure. Nicknamed the “Penny Bridge” after the toll for its early 19th century ancestor, the bridge had been replaced several times before this structure, the Meeker Avenue Bridge, was built in 1894. It was replaced by the Kosciuszko Bridge, a truss span, in 1939.

Opened in 1889, the Carroll Street Bridge is a rare retractable crossing, one of two in New York City and three (as of 2013) still in service in the United States. It opens diagonally, with its span slowly pulled into a reserved pocket on the Gowanus Canal’s western bank. Bridge openings are now a rare event, but were once quite common.

Completed in 1931, the Bayonne Bridge was at the time the longest steel arch bridge in the world. The design by Othmar Ammann and Cass Gilbert references the Hell Gate Bridge connecting Astoria, Queens and Randall’s Island.

Named for the rough tidal strait of the East River it traverses, the Hell Gate Bridge opened in 1917 and was the longest steel arch bridge in the world until 1931.