What’s in a Name?

For some, Manhattan’s Sixth Avenue is synonymous with the boxy skyscrapers of upper Midtown, where the thoroughfare is characterized by the bustle of business, grazing the western side of Rockefeller Center and Bryant Park. Others may associate Sixth Avenue with the more workmanlike blocks of the mid-thirties, where it forms the eastern edge of the Garment District and runs past Macy’s at Herald Square before continuing downtown through Chelsea into the handsome cast-iron emporiums of the Ladies’ Mile Historic District. Still others will recall its post-war rebranding as the Avenue of the Americas, a name bestowed in the 1940s as New York City, home to the new UN headquarters, aspired to a more global image.¹

But there is a different face to the avenue once you get a few blocks below Fourteenth Street. Rather than the high-rise development seen further north, here it cuts through fabric much older: the tangled streets of the West Village. These angled, irregular streets have always been notoriously difficult to navigate, and at the start of the twentieth century, New York City undertook two major street projects that would further complicate their layout: the extensions of Sixth and Seventh Avenues.

The 1915 creation of Seventh Avenue South is well known for its resulting jumble of oddly shaped lots and buildings, including the tiny Hess Triangle: a mis-measured scrap of land left over after the city used eminent domain to forcibly buy up the space required for the new thoroughfare.² A decade later, another avenue needed to be pushed through the Village — and beyond — to serve the city’s changing needs. In the final years of the 1920s, Sixth Avenue was lengthened to provide a route for new subway tracks, and to connect automobile traffic to the recently completed Holland Tunnel under the Hudson River. Although these changes were made in the service of commerce and improved transportation, they were also responsible for destroying appreciable portions of the surrounding blocks, displacing thousands, and forever changing the landscape of the adjacent neighborhoods.

Neighborhood Origins

To understand the areas that experienced these radical changes, it helps to know how they developed in the first place. The original residents of lower Manhattan were the Lenni Lenape, indigenous people whose ancestors had maintained a continuous presence here for thousands of years. Among their local settlements was Sapohanikan, where tobacco was grown along the Hudson at the northern edge of today’s West Village. Nearby Minetta Brook would have been their best source of fresh water.³

The 1624 arrival of the Dutch set the scene for European development and began a long series of displacements that would eventually drive the Lenape as far west as Oklahoma. Their trading-post town of New Amsterdam got its start at the southernmost tip of the island, but as early as the 1630s, governor Wouter van Twiller had occupied this pleasant stretch along the Hudson as his own tobacco plantation. Just inland were properties owned by African slaves who had been given partial freedom by the Dutch.⁴

The British takeover of what they came to call “New-York” in 1664 led to further expansion, and these areas soon became farmland owned by wealthy families. Riding north out of the city, one would have crossed a plank bridge over a little waterway that emptied into the Hudson farther west, which would later be expanded into a great ditch and used to drain the polluted Collect Pond — and whose route would eventually become today’s Canal Street.⁵

The area today known as Hudson Square was previously the northern portion of Trinity Church’s extensive landholdings, originally granted to them by the British crown in the late 1600s. A century later, the rural Richmond Hill estate of Abraham Mortier was located here, famously used as George Washington’s headquarters at the start of the American Revolution, and later the residence of Aaron Burr. And the adjacent neighborhood that we know as Soho began as the western portion of the Bayard family farm, prominent citizens since the time of Judith Bayard, wife of Dutch leader Peter Stuyvesant.⁶

Beyond these mostly uncultivated lands sat a portion of the Warren family estate, irregularly bounded on its northern edges by today’s Gansevoort Street and Greenwich Avenue. The descendants of Anglo-Irish naval hero and politician Peter Warren eventually sold their land off in 1790 to be divided up into streets and lots for residential development. Just a few decades later, the city’s rapid growth began to overtake the bucolic “Village of Greenwich” that had sprung up there.

The Commissioners’ Plan

In 1811, the Commissioners’ Plan set a new course for Manhattan’s future, prescribing a grid of numbered streets and avenues running the length of the island. These new roads would be broader than those of the past, with the avenues in particular being an impressive 100 feet wide. And the Commissioners’ office where the plan was devised was located just one block west of Sixth Avenue at the corner of today’s Bleecker and Christopher Streets “more than a mile north of the settled part of the city,” which still only extended as far uptown as Canal Street.⁷

The grid plan left most areas of existing development intact. Sixth Avenue, for example, was shown starting at Greenwich Avenue, the northeastern boundary of an existing grid of angled streets. Even so, reconciling existing property lines with the new system required a flurry of land purchases, sales, and divisions. It took surveyor John Randel Jr. six years just to lay out markers defining the corners of the new city blocks.⁸

The city quickly grew into its new street grid. By the 1830s, the pace of development had spurred an initial extension of Sixth Avenue just a few blocks south to Carmine Street, which would remain the avenue’s downtown terminus for another century. By the outbreak of the Civil War, the city had engulfed this once separate enclave and continued its relentless march uptown, forming a middle-class neighborhood set apart from its surroundings by the angled street grid.

In the 1870s, the construction of an elevated railroad line transformed the character of Sixth Avenue, replacing the horse-drawn trolleys and streetcars that once ran at ground level. Making its way up from the foot of Manhattan at Wall Street, the El turned at West Third Street and continued north along Sixth Avenue. As late as the 1880s, the legacy of Black land ownership, though greatly diminished, could still be seen nearby in the form of “Little Africa” along Minetta Lane.

By the turn of the twentieth century, this part of lower Manhattan had grown increasingly dense. Hudson Square became a busy commercial printing district, and today’s Soho became a center of light manufacturing and storage. Many of the former residences were replaced with larger and taller buildings. And the southern part of Greenwich Village had become home to recent immigrants, most of whom had come from southern Italy, giving the neighborhood a working-class character.

Traffic Now Forces Huge Street Cutting

In the early twentieth century, New York’s accelerating commercial growth placed new strain on the city’s infrastructure. The 1910 completion of new rail tunnels under the Hudson River, which linked New Jersey to Pennsylvania Station in Midtown, brought a surge of freight and passenger traffic into Manhattan and intensified congestion on the west side. To accommodate this new flow of people and goods, the city sought more direct routes to the docks and industrial districts along the Hudson. The 1915 extension of Seventh Avenue through the West Village met that need, opening a direct route to the waterfront and providing a path for the new Interborough Rapid Transit Company subway line below ground.

A decade later, Manhattan Borough President Julius Miller oversaw a plan to slice through these neighborhoods, this time linking Sixth Avenue to the new Holland Tunnel — the first underwater route for cars between Manhattan and New Jersey. This required extending Sixth Avenue, “which now stubs its toe and lies flat against the brick fronts of Carmine Street,” as The New York Times described it in 1926.⁹ Subway expansion was continuing apace, and the street extension served a dual purpose, providing a path for the IND — today’s A/C/E subway lines — which jog eastward at Greenwich Avenue before continuing along the southernmost stretch of Sixth Avenue.¹⁰

To achieve the necessary width for the tunnels and roadway, demolition extended into adjacent blocks at several points, leaving a jagged scar that stretched from just west of Washington Square Park all the way down past Canal Street. The avenue now pushed beyond the southern boundary of the West Village and it became the dividing line between today’s Soho and Hudson Square. In total, the extension stretched nearly a mile, cutting through fifteen blocks and removing from the map entirely the short lengths of Hancock, Congress, and Clark Streets. Every building in its way was demolished.

Although contemporary accounts stated that the extension ended at Canal Street, actual construction continued four blocks further into what is now Tribeca, following a curving course to Franklin Street.¹¹ There, the roadway and the subway lines merged gently into Church Street before continuing farther downtown.

Another Emigration

By the 1920s, the southern end of Greenwich Village was well known as an Italian American enclave. The stretch of Bleecker Street west of Sixth Avenue was a gourmand’s paradise lined with stores offering sausage, pasta, and cheeses. The blocks nearby were packed with tenements and rowhouses that were home to first- and second-generation immigrants. But the new roadway would, as one account put it, “cut like a sword through the knot of old streets” they inhabited.¹²

After the Sixth Avenue plan was approved, the city used eminent domain — a legal tool that allows the government to take private property for public use while compensating owners — to acquire the buildings along the planned extension. It took the city more than a year to acquire all the requisite parcels, and estimates of the displaced population ran to ten thousand residents.

The New York Times observed that “to ask families to uproot themselves and move to Brooklyn or the Bronx is like asking them to undertake another emigration,” and lamented that no plan had been made to provide suitable new housing for the displaced, leaving the community to its own devices.¹³ After successfully obtaining a one-month delay, residents of the doomed buildings were finally evicted in September 1926 to make way for the new avenue.

The neighborhood’s Italian identity survived the loss, but many whose homes were destroyed moved to more affordable quarters in the outer boroughs. Among other dislocations, the project required the removal of the Catholic Church of Our Lady of Pompeii, which moved only a short distance to a new building on the west side of today’s Father Demo Square at Carmine Street, notable for its distinctive corner bell tower.¹⁴

Cut and Cover

With the buildings vacated, demolition began. Block by block, walls and windows were peeled away, framing taken down, and debris carted off until gaps opened in the middle of blocks and the path of the new roadway started to take shape. Once the last structures were cleared, the route was ready for the next phase of work: construction of the underground subway line.

Elsewhere in Manhattan, deeper tunnels were typically bored through bedrock, a slow and costly process. Here, the shallower depth allowed a quicker, cheaper method known as “cut-and-cover.” Workers excavated the entire width of the street down to track level, built the tunnel enclosures and stations, then refilled the trench to the surface. Temporary wooden walkways allowed traffic to pass overhead during the long disruption, but for much of the construction period, the new stretch of Sixth Avenue remained a raw, open canyon.

By 1930, the new infrastructure was complete and the street restored to grade and paved. According to Manhattan Borough President Julius Miller, the entire project required 12,000 cubic yards of concrete, 100,000 square feet of sidewalk and 45,000 square yards of granite block pavement.¹⁵ That September, the newly finished avenue opened to great fanfare with a celebratory parade that ran from Carmine to Canal Street.

Impact and Legacy

After seeing the inefficient triangular lots left behind in the wake of the Seventh Avenue extension, the city took a different approach along the new portion of Sixth Avenue, setting aside those irregular spaces for small parks. Following local tradition, these three-sided plots are generally known as “squares” despite their triangular shape. In addition to Father Demo Square, a walk southward passes Winston Churchill Square, Little Red Square, and Father Fagan Park at Charlton Street. A sharp eye will spot several more angled green spaces before reaching the broad paved expanse of Duarte Square at Canal Street.¹⁶

Not only did the extension of Sixth Avenue require the outright demolition of many structures, it also left a number of formerly mid-block buildings newly exposed to street frontage. The blank side walls of these buildings can still be seen in some places. But over time, some owners adapted, adding windows, entrances, and even retail spaces along the avenue. In older Manhattan buildings, these solid walls usually abutted a neighboring structure, and windows were few and far between. Now that their buildings faced the open expanse of Sixth Avenue and were no longer constrained by fire codes, owners could cut new openings to let in light and air.

Among the many buildings reshaped by the Sixth Avenue extension, one of the clearest examples is 171 Sixth Avenue, a narrow six-story “dumbbell” tenement that originally faced Vandam Street.¹⁷ After the block was reconfigured, the owners unceremoniously bricked up the original entrance and tacked on a new central corridor giving tenants efficient access from the avenue side. They kept the small lightwell windows that once looked into adjacent bedrooms and bathrooms, and added generous new openings for the living areas, making for a disorganized new front facade. The small wedge of land that remained in front of the building was fenced in to form an irregular yard.¹⁸

Beyond these physical changes, the extension had a subtler impact on the entire length of the avenue. In Manhattan, addresses on the numbered cross-streets are generally consistent, extending predictably east or west from Fifth Avenue. But avenue addresses vary widely because each avenue begins at a different location. In 1929, the city renumbered every building on Sixth Avenue to account for the new southern stretch, shifting each address upward by about 350. The city had avoided a similar change on Seventh Avenue by dubbing its extension Seventh Avenue South, but the Sixth Avenue Association decided that “a good avenue was deserving of one complete name for its entire length.”¹⁹ Today, Sixth Avenue is the only numbered avenue extending south of Houston Street.

Sixth Avenue Today

The Sixth Avenue extension was anticipated to relieve congestion along the length of the avenue. And in January 1929, the president of the Sixth Avenue Association declared that the avenue was making “steady progress toward the position it should hold as one of the city’s important thoroughfares in the heart of Manhattan.”²⁰ But any positive impact was overshadowed by the onset of the Great Depression later that year. Sixth Avenue did not reach its full potential until after the 1939 demolition of its elevated railway, which was replaced farther uptown by today’s Sixth Avenue subway lines. That change triggered a real estate boom that transformed the northern half of Sixth Avenue into the familiar rows of skyscrapers and apartment towers we know today.

Although the southern stretch of Sixth Avenue has since seen its own share of new development, the scars left by the 1920s extension are still etched into its streetscape. The project’s jagged cuts through the West Village, Hudson Square, Soho, and Tribeca reveal the force required to drive a modern thoroughfare through the city’s eighteenth- and nineteenth-century urban fabric. The narrow irregular streets that surround it still hint at what this quiet corner of Manhattan once was, before the extension reshaped it forever.