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161 Madison

At the River’s Edge, Maiden Lane and the Development of Lower Manhattan

Recently, the story of the “Leaning Tower of New York,” came to our attention. Also known as “1 Seaport,” the building is located at 161 Maiden Lane on the corner of South Street. In 2018, a contractor on the new 60-story residential tower noted that the structure had begun to lean. In 2020, construction on the site halted when it became apparent the building’s foundation was unstable.

161 Maiden Lane from 180 Maiden Lane, May 2025. Photograph by the author.

Taking a dive into the rich collections of the Municipal Archives and Municipal Library revealed a long history of failed development at this location. This week, For the Record peels back the layers of history that have made this such a problematic site.

This map from 1909 attempted to show the natural contours of Smith’s Vly and the location of Cornelius Clopper the blacksmith’s residence. “Amsterdam in New Netherland, 1653-1664.” Townsend MacCoun, 1909. Lionel Pincus and Princess Firyal Map Division, The New York Public Library.

In the early 1600s, Dutch settlers in New Amsterdam called Maiden Lane Maagde Paetje, a meandering path along a stream in Smit’s Vly. In the Dutch language, a Vly, or Vlaie, refers to a low-lying often marshy area next a stream. Later, English colonial settlers Anglicized the name to Smith’s Fly. Maagde Paetje or Maiden Lane (its meaning the same in Dutch as in English) may have come from the Dutch girls who washed their family’s clothes in the stream. In the Dutch colonial days Maagde Paetje would have ended at what we now call Pearl Street, which was then the river’s edge. Cornelius Clopper the Blacksmith had his forge there, the smith of Smith’s Fly.

The Fly Market was established on Maiden Lane in the 1690s. “Fly Market,” 1816. George Hayward for Valentine’s Manual for 1857. NYC Municipal Library.

By the late 1600s English colonists had used landfill to extend the shoreline to Dock Street, now known as Water Street. Around this time the Common Council approved the construction of the Fly Market on Maiden Lane from Pearl Street (then called Queen Street) to Dock (Water) Street. The 1754 Maerschalck Plan shows a further extension in this area to Burnets Key, a boat slip and dock. Burnets Key would become Front Street, built out with fill on either side to become the new eastern edge of downtown.

The Maerschalck Plan of 1754 shows the expansion of the shoreline and the extension of Maiden Lane to a boat slip at Burnets Key. Burnets Key would become Front Street. Map courtesy The Library of Congress.

By 1810, the City had expanded even further to South Street, which became the main seaport of 19th Century New York. In 1822, the first Fulton Market was constructed further north, and the Fly Market was demolished. A few years later, the Great Fire of 1835 destroyed several blocks below Wall Street, but spared Maiden Lane.

South from Maiden Lane, 1828. George Hayward lithographer, for D.T. Valentine’s Manual of 1854. NYC Municipal Library. 

1885 Atlas of Manhattan. The Piers were later renumbered and Pier 18 became 14. NYC Municipal Archives.

The first buildings at Pearl Street and Maiden Lane may have been wooden. Although there was legislation requiring brick construction as early as 1766, until the Great Fire of 1835 buildings built on landfill were exempt because it was unknown if the new land could support them. But by the mid-1800s the area would have been four- or five-story brick buildings used as shops, counting houses, warehouses and sailor’s lodgings.

In 1916, five brick buildings were torn down at the corner of Maiden Lane and South Street to make way for a six-story concrete warehouse designed by architects Jonathan B. Snook & Sons. According to the Certificate of Occupancy from 1918, the first floor of 161 Maiden Lane was occupied as a “store,” the second as a “factory, printing,” the third for “storage,” fourth floor, “office and storage,” and the sixth floor, “sales.” A solid industrial loft building, typical of the era, as it appears in the Tax Photograph from 1939.

161-169 Maiden Lane, ca. 1939. 1940s Tax Department photographs. NYC Municipal Archives. This warehouse was built in 1919, replacing five smaller buildings. It was demolished in 2007.

Tracts and Farms with Street Changes, County of New York, Plate 2. Reindexing Department Map Division, 1917. NYC Municipal Archives.

By the 1930s the East River waterfront was on a downward trajectory although Piers 14 and 15 at the end of Maiden Lane were still in use at least until the 1960s. The piers handled small cargo ships, and the Fulton Fish Market still received fishing trawlers, but the larger ships coming into New York needed a deep-water port and favored the westside piers on the Hudson. A trend that began in the latter half of the 1800s. New ports in New Jersey and containerization pushed the area into further decline in the 20th Century.

A cargo ship can be seen docked next to Pier 14 at the foot of Maiden Lane in this aerial view of Lower Manhattan and the East River Piers, November 5, 1953. Department of Marine and Aviation Collection. NYC Municipal Archives.

East River Piers—South Ferry to Pier 14, November 22, 1961. Department of Ports and Trade/Marine and Aviation photographs. By 1961 many of the East Side Piers had been abandoned although Piers 14 and 15 by Maiden Lane were still operational. Today only the helipad, and Piers 11, 15, 16, and 17 remain.

In the 1950s, new glass skyscrapers started to replace the old sailmaker lofts and push out the artists who had taken them over. Urban planners floated various schemes to revitalize the area. In 1960, the Downtown Lower Manhattan Association proposed a World Trade Center for the area. It would have stretched from Water Street to South Street from Fulton to Old Slip. If built, 161 Maiden Lane would have been razed. Eventually the World Trade Center site was moved to the west side, destroying the neighborhoods known as Little Syria and Radio Row.

World Trade Center: A Proposal for the Port of New York, 1960. Downtown Lower Manhattan Association, Inc. NYC Municipal Library, vertical files.

World Trade Center: A Proposal for the Port of New York, 1960. Downtown Lower Manhattan Association, Inc. NYC Municipal Library, vertical files.

World Trade Center: A Proposal for the Port of New York, 1960. Downtown Lower Manhattan Association, Inc. NYC Municipal Library, vertical files.

The Lower Manhattan Plan of 1966 saw the potential to expand Lower Manhattan once again in two “opportunity areas,” the West Side, which would become the World Trade Center and Battery Park City, and the East Side. Wallace, McHarg, Roberts and Todd. Office of Lower Manhattan Development.

In 1965 and 1966, the New York City Planning Commission developed new plans to expand Lower Manhattan once again in two “opportunity areas.” The West Side opportunity area became the World Trade Center and Battery Park City. The East Side development would have largely eliminated South Street with massive residential and commercial complexes stretching from the Battery Maritime Building up to the Brooklyn Bridge, from Water Street to a new bulkhead further into the East River. Park land would cover the shoreline encompassing the Manhattan tower of the Brooklyn Bridge. In January 1967, Mayor John V. Lindsay created the Office of Lower Manhattan Development “to coordinate and integrate projects in the Lower Manhattan area, including the World Trade Center and the Civic Center, into the general framework of the Lower Manhattan plan.”

The Lower Manhattan Plan, 1966. Whittlesey Conklin and Rossant, Alan M. Voorhees & Associates, and Wallace McHarg Roberts and Todd for the New York City Planning Commission. NYC Municipal Library. 

South Street and Maiden Lane sit at the center of this drawing. The Lower Manhattan Plan, 1966. Whittlesey Conklin and Rossant, Alan M. Voorhees & Associates, and Wallace McHarg Roberts and Todd for the New York City Planning Commission. NYC Municipal Library.

The building at 161 Maiden Lane was narrowly excluded from preservation. South Street Seaport Historic District Designation Report, 1977. Landmarks Preservation Commission. https://s-media.nyc.gov/agencies/lpc/lp/0948.pdf

Preservationists started to push back against the massive developments, and in 1967 the founders of the South Street Seaport Museum convinced the City to spare many of the remaining 19th-Century buildings from the wrecking ball. In 1968, the lightship Ambrose was donated to the Museum, its first historic ship. In 1970, the tall ship Wavertree arrived to begin its long restoration.

In 1976, the Office of Lower Manhattan Development was consolidated along with three other offices to form the Mayor's Office of Development. In 1977 the Landmarks Preservation Commission formally designated the South Street Seaport Historic District, preserving a stretch of buildings along South Street below the Brooklyn Bridge. It stopped just short of Fletcher Street, the rear of 161 Maiden Lane. Piers 15, 16 and 17 were redeveloped as part of the South Street Seaport, but all the piers below them, with the exceptions of Pier 11 and the heliport, languished and were demolished. In 1980 the Seaport Museum and the Public Development Corporation (a predecessor agency to the NYC Economic Development Corporation) commissioned Beyer Blinder and Belle to create a master development plan for the Seaport Historic District as a dining and tourist destination.

Aerial view of the South Street Seaport, ca. 1974. Suzanne O’Keefe, Department of City Planning.

Growth of Manhattan Island, 1650-1980. The projected 1980 expansion never occurred on the east side. The Lower Manhattan Plan, 1966. Whittlesey Conklin and Rossant, Alan M. Voorhees & Associates, and Wallace McHarg Roberts and Todd for the New York City Planning Commission. NYC Municipal Library.

161-69 Maiden Lane, ca. 1985. 1980s Tax Department photos. NYC Municipal Archives.

In 1999 yet another proposal was floated to develop the area. Fresh off of the success of the Guggenheim Museum Bilbao, the Solomon R. Guggenheim Foundation proposed another Frank Gehry designed curvilinear museum that would sit in the East River along South Street from Wall Street to Maiden Lane, replacing Piers 9, 13, and 14. Heated public debate ensued, but following the attacks of 9/11 in 2001 priorities shifted to rebuilding the World Trade Center and in 2002 the plans were scrapped.

Model of proposed Downtown Guggenheim Museum designed by Frank Gehry. Photo by David Heald. Mayor Rudolph Giuliani collection. NYC Municipal Archives.

Hurricane Sandy Surge Boundary Final, October 22, 2012. arcgis.com

Sometime around 2007, demolition began on 161-169 Maiden Lane according to permits issued by the Department of Buildings. The reasons for the demolition are unclear. Nothing new was built and the property became a parking lot.

On October 22, 2012, Hurricane Sandy hit the east coast. The resulting storm surge reached a high-water mark along Pearl Street and pushed up Maiden Lane as far as William Street, reminding New Yorkers where the true natural boundaries of their city are located. Despite this, a year later in 2013, the Fortis Property Group paid sixty-four million dollars for the parking lot at the corner of Maiden Lane and South Street. Their ambitious plan was to build a 60-story residential tower on a narrow lot that had still been the East River in the 1700s and had been under water just a year prior.