A Remarkable History of the Bowery

Few streets in the world can boast such a colorful history as the Bowery — Manhattan’s oldest thoroughfare. Physically it runs through historic neighborhoods of Little Italy, Chinatown, East Village, and Lower East Side; metaphorically, it goes through each and every period of New York’s complicated history.

The Bowery was once a Native American trail that extended the length of Manhattan. During the Dutch times (1624-1664), it connected the city of New Amsterdam with the farmlands that lay to the north of the town. In fact, the name Bowery is the Anglicized form of Bouwerij, the Dutch word for farms.

Under the English (1664-1783), it was a part of Boston Post Road, lined with expensive mansions that belonged to prominent families like the Bayards and de Lanceys.

In 1783, when the Revolutionary War was over, George Washington marched his triumphant troops down the Bowery and raised a glass or two to the American victory at the Bull’s Head Tavern, once located at 48 Bowery.

After the independence, around the 1780s – 1830s, the Bowery became a butcher’s district. Edward Mooney house (1785) at 18 Bowery, the city’s oldest brick house (!), is still standing!

Between the 1830s and 1860s, the Bowery turned into a respectable elegant street inhabited by New York’s wealthy merchant class, only to lose its respectability by the 1870s, when it transformed into a commercial area with cheap lodgings and flophouses. The change happened due to a flood of new immigrants arriving to New York City, settling in the area, and pushing upper-class New Yorkers to move northward. Single-family dwellings were converted to tenements, and the mansions had given way to low-brow concert halls, brothels, beer gardens, pawn shops, and flophouses. The Bowery became the turf of one of America’s earliest street gangs, the native Bowery Boys. 

It’s around this time, in the 1870s, when the Bowery entered its most colorful period. It became NYC’s first entertainment district featuring tap dance, minstrelsy, vaudeville, and Yiddish theater. Separated by half a century, Stephen Foster and Irving Berlin, two greatest American songwriters, lived and worked on the Bowery. Foster wrote his last song and spent his last days at the New England Hotel at 30 Bowery, dying in 1864 at age 37. In the early 1900s, a teenaged Irving Berlin sang for pennies while living on the street and in Bowery flophouses. His career was launched when he met Chuck Connors — the self-described Mayor of Chinatown — at Barney Flynn’s Saloon (18 Bowery), who helped him get his first gig as a singing waiter in Chinatown. “I got my musical education in the Bowery,” — Irving Berlin remembered.

The Bowery was one of America’s first avenues with streetcars, trains, and electricity, which explains its spectacular nightlife that became renowned to travelers around the world. During this period, the Bowery became a major theater and nightlife district.

It’s the next development of transportation that led to Bowery’s demise. The Third Avenue elevated line that opened in 1878 transformed the street into a dark and noisy area unsuitable for its middle-class inhabitants, who eventually fled this part of town. Attracting the poor and destitute, the Bowery descended into the center of social ills and gained a national reputation as a “Skid Row” and a “Thieves’ Highway.”

It reached its lowest point a century later, in the 1970s, when it became a downright scary, desolate place with drug addicts and scores of homeless living on the street.

The Bowery started as a Lenape trail and turned into a Dutch farm road. When the Revolutionary War ended, Washington’s troops marched down the Bowery. Herds of cattle stomped it, heading for the Collect Pond. It developed into the city’s working-class entertainment district where tap dance, minstrelsy, Yiddish theater, and vaudeville were born. It went through a rough period as a home for gangs, thieves, and drug addicts. Today, the Bowery got gentrified; its streets are lined with many restaurants and host fancy hotels. Still, it preserves its authenticity through its historic architecture and a unique location at the nexus of Little Italy, Nolita, Chinatown, SoHo and the Lower East Side.