Little is known about Samuel Willoughby, the immigrant businessman for whom Willoughby Avenue and Willoughby Playground are named. He moved to the United States when he was 19 and entered the dry goods business. In 1830, he married Margaretta Duffield, the daughter of one of Brooklyn’s wealthiest families. According to business directories at the time, he founded the Brooklyn Bank in 1832 and sat on the board of directors of the Brooklyn Fire Insurance Company and the Long Island Insurance Company. Willoughby also developed business property in downtown Brooklyn on a triangle bounded by what are now Pearl, Fulton and Willoughby Streets.
Willoughby Avenue opened between Franklin and Nostrand Avenues in 1851, in 1867 it was expanded between Yates Street (now Marcus Garvey Boulevard) and Broadway, and the final section between Tompkins and Throop Avenues was added in 1871.
In an 1896 petition to prevent the renaming of part of Willoughby Avenue, local merchants explained that “Willoughby street [sic] is one of the very oldest streets in our city. It was, at one time, the most fashionable street, having for residents the Willoughbys, Duffields, Rockwells, and Princes, the men who owned Brooklyn.” These merchants were not successful however, and the street was renamed Joralemon Street west of Borough Hall, after Teunis Joralemon, a landowner who helped develop Brooklyn Heights in 1803.
Willoughby Playground is located in the Bedford-Stuyvesant neighborhood on Tompkins Avenue between Vernon and Willoughby Avenues. North-central Brooklyn was Dutch farmland in the 17th and 18th centuries. In the early 19th century the farmland was divided into housing lots and sold to newly-freed blacks who settled the area. Bedford-Stuyvesant was once two separate communities known as Bedford Corners and Stuyvesant Heights. They came together to form what is now the largest African-American community in New York City.
The City acquired the land for the park in 1963, and it opened along with P.S. 23 in 1967. Formerly known as P.S. 23 Playground, the park was designated Willoughby Playground by Parks in 1986. The playground was renovated in 1997-98 with $277,046 from Mayor Giuliani and $233,726 from Borough President Howard Golden. The renovation provided new play equipment with safety surfacing, handball courts, and improved pavements, paths, sidewalks, fences, and guiderails. In addition, basketball courts, benches, a spray shower, a comfort station, a flagpole with yardarm, a camel sculpture, London planetrees (Platanus x acerifolia) and a decorative gate make this playground complete.