James Nevius is the author of three books about New York City, the most recent of which is Footprints in New York: Tracing the Lives of Four Centuries of New Yorkers.

Every generation has defined Greenwich Village differently—sleepy suburb, elite residential enclave, America's Left Bank, Sex in the City streetscape—but the one constant for over two centuries has been the neighborhood's tangle of streets, which defy logic and sometimes surprise even longtime residents. Purposefully left off John Randel's 1811 Manhattan street grid, the core of the West and South Village lies along even older thoroughfares: Christopher Street, which cut inland from the pier; Greenwich Avenue (known in the colonial era as Monument Lane), and, most significantly, Bleecker Street, which was an important road even before it cut through Anthony Bleecker's farm.

The far western edge of what we call Greenwich Village was a Native American settlement/fishing camp known as Sapokanican, a name which may or may not refer to tobacco fields in the area. Certainly, by the time the Dutch arrived in force in the 1620s, tobacco was on their minds, and the Dutch West India Company's director-general, Wouter Van Twiller, acquired a large parcel of land in the area in 1633 to cultivate the cash crop. The Dutch began referring to the small settlement as Noortwijck ("north village"), a reminder that it was the first village where ships could put in when sailing north on the Hudson River from New Amsterdam.

For much of the seventeenth and eighteenth centuries, the Hudson River was the primary mode of travel to Noortwijck; the only other route north, the Bowery ("farm road") ran too far to the east. Some early maps also show a "Road to Greenwich" (today's Greenwich Street) hugging the coastline, but it was often flooded, rutted, and not really viable. At some point after the British took over New Amsterdam in 1664, Noortwijck was renamed Greenwich, but the reasons behind this are murky. It may simply be named after Greenwich, England, or it may be a corruption of another Dutch moniker, Greenwijck ("pine village").

As the population of Manhattan grew, Greenwich Village became a place for wealthier New Yorkers to summer. The most famous country estates were Richmond Hill—home to John Adams when New York was the seat of government, and then later to Aaron Burr—and the home of Admiral Peter Warren, at what would one day become the block bounded by Perry, Charles, West 4th Street, and Bleecker. In 1748, a large tract west of the Bowery was acquired by Elbert Haring and his land (mislabeled "Herrin") appears on the 1767 Ratzer map with a small road running through it; that road is the first evidence for what is today Bleecker Street—and the path may well have pre-dated the Haring family's purchase.

By 1797, when the city hired surveyors Joseph-François Mangin and Casimir Goerck to create a comprehensive city map, the area closest to the Bowery was in the hands of Anthony Lispenard Bleecker. The Mangin-Goerck plan, produced in 1801, was more ambitious than the city had bargained for, adding streets where none existed and charting, for the first time, the course for the city's northward growth. Though the common council rejected the Mangin-Goerck survey (instead appointing the commission that would produce the street grid we have today), many of its features were incorporated, including the present course of Bleecker Street. From the Hudson to what is now Sixth Avenue it was labeled Herring Street (undoubtedly a corruption of Haring); east of Sixth Avenue it became St. David Street, and the small section from Broadway to the Bowery was labelled, for the first time, Bleecker. In 1808, Anthony Bleecker deeded his twenty-acre farm to the city, and by 1817, when lots were being auctioned off, the Bleecker name extended all the way to the present Sixth Avenue; in 1829, as part of a plan to streamline Village street names, Herring Street was dropped and Bleecker became the name of the entire thoroughfare.

The oldest house still standing on Bleecker, No. 329, was built sometime between 1802 and 1810 (when it was still Herring Street) at the corner of Christopher. This two-story building, which housed William Patterson's grocery store on the ground floor, would have been wider originally; soon after Herring Street became part of Bleecker, the roadbed was widened (warning: PDF!) and the edge of the grocery lopped off and replaced. When Patterson opened his store, this intersection would have been the center of the old Village, a sleepy backwater with no churches and a one-room schoolhouse. All of that was about to change.

Although the publication of the Commissioners' Plan of 1811 provided a framework for future growth into the newly charted streets north of Fourteenth Street, the nucleus of the first wealthy neighborhood outside the old city was Bleecker Street. It and other streets clustered around Broadway and the Bowery—Lafayette, St. Marks, Great Jones, and Bond—came to be known as the neighborhood "above Bleecker," from which bankers, brokers, and downtown merchants would commute each day. In 1821, James Roosevelt (a lawyer, sugar refiner, and great-grandfather of FDR) built an elegant townhouse (right on the corner of Bleecker and Crosby, now home to the Bleecker Street Bar. A year later, a deadly yellow fever outbreak sent scores of New Yorkers to Bleecker Street's western precincts, and almost overnight what had been a village disconnected from the rest of the city became a real suburb.

In 1826, the large graveyard was reopened as Washington Square, drawing more people to the area. By the time the famous homes on Washington Square and Lafayette Street were finished in the early 1830s, the bulk of New York's high society had moved to the Village.

While Colonnade Row and Washington Square are the area's most famous housing developments, Bleecker Street had a number of upscale terraces. The "first and finest" of these, according to Village historian Luther S. Harris, was LeRoy Place, the name of the block of Bleecker between Greene and Mercer Streets. Nearby Carroll Place was built by developer Thomas E. Davis in 1831 on the block of Bleecker east of Thompson, and the similar DePau Row opened a year later a block farther west.

While LeRoy Place and DePau Row are long gone, five buildings from Carroll Place still stand, their original elegance apparent despite later alterations. Nos. 144 and 146 on the south side of the street, and Nos. 145-149 (which now house, among other things, the famous club The Bitter End) face them on the north side. Among Carroll Place's illustrious residents was author James Fenimore Cooper, who lived at No. 145 in 1833 before decamping to another Davis development on St. Marks Place.

By the 1850s, the character of Bleecker Street was changing. When the Civil War Draft Riots swept the city in July 1863, police and protesters clashed on Bleecker Street. The U.S. Army's Eastern District office—the ultimate target of the mob's wrath—was housed at No. 37 Bleecker, in a building that still stands.

As wealthier residents moved north before and after the war, the once-elegant homes on Bleecker Street became the center of the boarding-house trade. In the words of the 1857 treatise The Physiology of New-York Boarding-Houses, any building "that is not a shop may be safely assumed" to be devoted to "the accommodation of the boarding public. On summer evenings not a stoop but has its knot of male boarders 'cooling off' after the heat of the day; not an open parlor-window but frames loveliness…the whole thoroughfare, indeed, presenting a continuous gallery of metropolitan manhood and femininity." As manufacturing filled up present-day SoHo and the area east of Washington Square, these boarding houses would have been conveniently located for workers who could only afford to commute on foot. In 1872, the hysterical (in every sense of the word) guidebook, Light and Shadows of New York Life, compared Bleecker Street and its vile "third-rate boarding houses and restaurants" to Paris's Latin Quarter, calling it New York's "headquarters of Bohemianism"—a description the Village has yet to shake, nearly a century and a half later.

Adding to the Bohemian nature of the street was the influx of Italians after that country's unification in 1870. While the number grew slowly (there were only 3,017 Italians in all of New York City in 1870), by 1920 over half of the residents of the Village had either been born in Italy or were first-generation Italian-Americans. This demographic shift forever altered the complexion of Bleecker and the surrounding streets. Not only were the boarding houses turned into tenements, but the shops, restaurants, and cafes were primarily run by Italians, and catered to an eclectic crowd of working-class Italians who dined and drank side-by-side with the writers, poets, and Bohemians drawn from other parts of the Village. Perhaps the most famous eatery, Mori's, was headquartered in old Carroll Place homes at Nos. 144-146. Meanwhile, DePau Row was torn down in 1895 so that Mills House No. 1, a model tenement designed by Ernest Flagg, could go up in its place. Housing only single men, the hotel could accommodate 1,500 lodgers at a time; these men were locked out during the day to encourage them to find work. Many ended up in the bars over on the Bowery, where a nickel beer came with access to the buffet (hence the signs "No Free Lunch"), further hastening that street's identification as Manhattan's skid row.

As the Italian character of the street grew, the centerpiece of the neighborhood was the parish of Our Lady of Pompeii, established in 1892 and now located at the corner of Bleecker and Carmine, which continues to serve as the focal point of the Italian presence in the South Village. The blocks of Bleecker Street west of Father Demo Square (named for the longtime pastor of Our Lady of Pompeii) still house multigenerational Italian businesses, from the famous John's Pizza to Porto Rico Importing Company to Ottomanelli butcher shop.

By the 1950s, Bleecker rivaled Mulberry in the public's imagination as the center of Little Italy, and in 1954, Gian Carlo Menotti wrote The Saint of Bleecker Street, a grand opera about the neighborhood that won him the Pulitzer Prize. Around the same time, the Amato Opera company premiered its first work in the parish hall of Our Lady of Pompeii; soon, the Amatos had leased a theater space at 159-161 Bleecker to be the opera company's headquarters. (In 1964, the company moved to the Bowery, where it remained until it closed in 2009.)

But the character of the neighborhood was changing again. Middle-class Italians were leaving Manhattan altogether for the outer boroughs, Long Island, and New Jersey. A new generation of writers—the Beats—were drawn to the area's cafes. Allen Ginsberg lived at Mills House No. 1 in 1951 at the rate of $2 a day; he hung out at Cafe Figaro at Nos. 184-186 (now gone, though you can still see the original awning on the second-floor windows) with Williams S. Burroughs, Greg Corso—who'd been born down the street—Jackson Pollock, James Baldwin, Bob Dylan...the list is endless. One Figaro regular was Miles Davis, who played the Village Gate, a club that opened in the basement of the Mills House in 1958. (It, too, is only survived by a second-story sign.) Another hangout in the building was the Mills Tavern, where Bob Dylan recalled in his autobiography, Chronicles, Volume One, that he and other "basket-house singers would bunch up, chitchat and make the scene."

Bleecker Street was so central to the music scene that Paul Simon named a song after it on Simon and Garfunkel's debut album in 1963; two years later, Fred Neil—who'd given Dylan his first break—released the album Bleecker and MacDougal, a signpost directing wannabe folk singers to the epicenter of the Village. Music venues proliferated: The Bitter End at No. 147 opened its doors in 1961, and was later the place that Dylan planned his Rolling Thunder Review. Nearby, the Cafe Au Go Go (now gone) shot to fame soon after its opening in 1964, when Lenny Bruce was convicted for using obscenities in his standup act. (Bruce died before his attorneys could successfully appeal the verdict.)

As music was coming to define Bleecker Street near MacDougal, the area further east was being bulldozed. In the mid-1950s, everything between Bleecker and Houston Street bounded by Mercer Street and West Broadway (including any remains of LeRoy Place) was torn down as part of a massive Title I housing project under the aegis of Robert Moses. The new Washington Square Village—now owned by NYU—contained nearly 1,300 apartments and effectively killed Bleecker Street. Today, Bleecker exists in two sections: the small area between the Bowery and Broadway, and the area west of LaGuardia Place. Everything between has withered.

The most recent chapter in the history of Bleecker Street has mirrored the city's overall homogenization during the past two decades. In the 1960s, Mori's restaurant became the Bleecker Street Theater, an independent movie house that held on until 1990—but the space is now a Duane Reade. West of Seventh Avenue in what were once only residential blocks, higher-end shops like Marc Jacobs, Calvin Klein, and Magnolia Bakery—which rocketed to fame thanks to Sex and the City—are the only ones that can keep pace with the rising retail rents. For years, Abbie Hoffman's Yippies were located near the Bowery at 9 Bleecker, now becoming a boxing gym.

Still, too many remnants of old Bleecker Street persist for it to lose its charm. The old Amato Opera space at No. 159—which later housed the Circle in the Square theater—is now The Market NYC, a collective of artisan shops reminiscent of the small stores that once lined that section of Bleecker. The Village Gate may be gone, but Le Poisson Rouge curates eclectic musical offerings in the same space, and the Italian cafes on and around Bleecker feel more authentically Italian than anything on nearby Mulberry Street.

In "Bleecker Street," Simon and Garfunkel sang, "A poet reads his crooked rhyme / Holy, holy is his sacrament / Thirty dollars pays your rent / On Bleecker Street." The thirty-dollar rent may be long gone (even Ginsberg paid twice that at Mills House, which was essentially an SRO), but the poetry is still there, woven into the bricks and mortar of the buildings by generations of New Yorkers.

· Bleecker Street coverage [Curbed]

· Curbed Features archive [Curbed]