William John “Bill” Cunningham (1929-2016) was a long-time New York Times photographer and journalist known for his “On the Street” and “Evening Hours” columns. As much a cultural anthropologist as he was a fashion photographer, Cunningham was known for candid street or event photographs of New Yorkers that depicted up-to-the-minute fashion trends. Among Cunningham’s most frequent locations to photograph his candid shots was the corner of Fifth Avenue and Fifty-Seventh Street and at the “up-to-twenty galas” he attended each week.

To achieve his telling photographs, Bill Cunningham often circulated around the city on a bicycle. In temperate weather he wore a French workers’ jacket. The bicycle here is one of thirty Cunningham owned over his many years of activity. It was made by Biria, a German manufacturer of upright bicycles designed for short rides on flat, urban surfaces. As indicated by the “Ciel Bicycles” tag also affixed to the bicycle, Cunningham probably purchased it at Ciel Bicycles, “the flagship New York City store of Biria” located at 360 East 65th Street. The jacket is also one of several he regularly wore. The Nikon camera, too, is one of several owned by Cunningham, and was probably used through the end of his career.

Parking meters have been an emblem of New York City street life since 1951, when the first meters were introduced to ease congestion and provide revenue. In 2006, the last mechanical parking meter was withdrawn from service as the city completed its conversion to battery-powered digital meters, which are more accurate, reliable, and vandal resistant than the older spring-loaded devices. On December 20, 2006, the last mechanical meter was retired from its spot on the southwest corner of West 10th Street and Surf Avenue in Coney Island, Brooklyn. Iris Weinshall, then the city's transportation commissioner, remarked to a New York Times reporter that the manual meter had gone the way of the subway token and noted, "This type of meter will go into museums, just like other memorabilia of the city." In the late 1980s, the city boasted 69,000 mechanical meters on its streets, but it stopped purchasing them about 10 years ago. In 1995, the city first began using digital meters, and the following year they introduced multispace meters, called Muni-Meters, that accept prepaid parking cards. This example is a one-hour meter that accept only quarters: one quarter buys 20 minutes of parking.

Parking meters have been an emblem of New York City street life since 1951, when the first meters were introduced to ease congestion and provide revenue. In 2006, the last mechanical parking meter was withdrawn from service as the city completed its conversion to battery-powered digital meters, which are more accurate, reliable, and vandal resistant than the older spring-loaded devices. On December 20, 2006, the last mechanical meter was retired from its spot on the southwest corner of West 10th Street and Surf Avenue in Coney Island, Brooklyn. Iris Weinshall, then the city's transportation commissioner, remarked to a New York Times reporter that the manual meter had gone the way of the subway token and noted, "This type of meter will go into museums, just like other memorabilia of the city." In the late 1980s, the city boasted 69,000 mechanical meters on its streets, but it stopped purchasing them about 10 years ago. In 1995, the city first began using digital meters, and the following year they introduced multispace meters, called Muni-Meters, that accept prepaid parking cards. This example is a one-hour meter that accept only quarters: one quarter buys 30 minutes of parking.

The "Lady Washington" was built in 1851 and used by the Lady Washington Engine Co. No.1 in Morrisania until 1874, when Morrisania was annexed to New York City.

Checker cabs, synonymous with New York, ferried passengers around the city from 1922 until the last cab was retired in 1999. From 1956-1982, the Checker Cab Manufacturing Company in Kalamazoo, Michican produced the classic 50's design four-door sedan, featuring high doors and auxiliary jump seats, which provided ample seating for up to five passengers with baggage. This cab, christened "Betsy II" by its driver Harold Winderbaum, carried passengers from 1982 to 1992.

According to the donor, his son was in the salvage business. He broke down old subway cars, and this bell was retrieved from one of these cars. This type of bell was used on one of the old NYC elevated train cars to signal the start of a train ride.