The name comes from the Dutch word for farm. When the Dutch colonized Manhattan, they called the Lenape trail "Bouwerie road" because it connected the farmlands on the outskirts to the settlement at the island's southern tip. In 1654, the Bowery's first residents arrived at Chatham Square: ten freedmen and their wives, who set up cabins and a cattle farm. Petrus Stuyvesant, the last Dutch governor of New Amsterdam before the English took control, retired to his Bowery farm in 1667. After his death in 1672, he was buried in his private chapel. His mansion burned down in 1778, and his great-grandson sold the remaining chapel and graveyard to a church -- St. Mark's Church in-the-Bowery, which still stands on the site at Second Avenue and 10th Street, making it one of the oldest sites of continuous worship in New York City.

By the early 1800s, the farms were gone and the Bowery was transforming into something grander: a broad boulevard where industrialists, philanthropists, and theatrical impresarios built their fortunes. Peter Cooper, who founded Cooper Union, lived along the Bowery. The Bowery Theatre became one of the city's premier stages, though its audience was working-class, drawn from the immigrant-heavy Five Points neighborhood nearby. George Washington stopped at the Bull's Head Tavern on the Bowery for refreshment before riding to the waterfront to watch the British depart in 1783. As late as 1869, the street still held the "reputation of cheap trade, without being disreputable" and was considered "the second principal street of the city," behind only Broadway.

The Bowery's slide began at the edges. It marked the eastern border of Five Points, Manhattan's most notorious slum, and became the turf of one of America's earliest street gangs, the nativist Bowery Boys. By the 1890s, the street was a center for prostitution rivaling the Tenderloin district. Bars catering to gay men and lesbians operated openly at various social levels -- from The Slide on Bleecker Street, known as New York's "worst dive," to Paresis Hall on 5th Street. Historian George Chauncey has documented how gay subculture was more visible on the Bowery and more integrated into working-class male culture than it would be for generations to come. In the spirit of social reform, the first YMCA opened on the Bowery in 1873, and the Bowery Mission was founded in 1879, where it continues to operate today.

From 1878 to 1955, the Third Avenue Elevated railway ran directly above the Bowery, casting its iron shadow over the street and accelerating its transformation into skid row. "It is filled with employment agencies, cheap clothing and knickknack stores, cheap moving-picture shows, cheap lodging-houses, cheap eating-houses, cheap saloons," writers in The Century Magazine observed in 1919. "Here, too, by the thousands come sailors on shore leave -- notice the 'studios' of the tattoo artists -- and here most in evidence are the 'down and outs.'" Prohibition killed the saloons. Restaurant supply stores moved in, and many remain today. Theodore Dreiser set the suicide of a main character in a Bowery flophouse in his novel Sister Carrie. The word "Bowery" became shorthand for destitution itself.

The vagrant population declined after the 1970s, partly through the city's deliberate efforts to disperse it. What came next was the familiar New York story of gentrification, but on the Bowery it carried a particular irony: luxury apartments and a Whole Foods Market rising on a street that had been synonymous with homelessness for a century. CBGB, the punk rock club at 315 Bowery that launched the Ramones and Talking Heads, closed in 2006 and became a John Varvatos fashion store. In 2008, AvalonBay Communities opened its first luxury complex on the street. The displacement has not been painless -- tenants at 83-85 Bowery were forced out in January 2018 in freezing temperatures and went on a hunger strike. Between Houston and Delancey, the Bowery still serves as New York's principal market for restaurant equipment. Between Delancey and Grand, it sells lamps. The oldest road on Manhattan Island keeps reinventing itself, as it has for four hundred years.