A walk down the longest true alley in Manhattan

New York was never the kind of city that built alleyways behind its buildings.

As Manhattan grew in the 18th century, real estate was deemed too valuable to waste on alleys. Why not stack buildings behind each other and make more money, right?

That’s likely why new alleys were generally excluded from the Commissioners’ Plan, the 1811 street grid that mapped out the future city plan of the entire island.

Alleys that already existed on city maps were clustered downtown. Some of these still survive, like Exchange Alley, a sliver connecting Trinity Place and Broadway. There’s also Mechanics Alley, running two blocks alongside the Manhattan Bridge approach.

But one new alley was fully laid out and named six years after the street grid plan: Cortlandt Alley.

Today, this shadowy and atmospheric lane runs three blocks from Franklin Street to Canal Street, earning the title of the longest true alley in Manhattan.

“In 1817. John Jay, Peter Jay Munro, and Gordon S. Mumford laid out the alley through their property between White and Canal Streets,” states the 1992 report designating the east side of Tribeca a historic district. The men named it after Jacubus Van Cortlandt, a descendant of the landowning Dutch colonial family.

It’s hard to see it on this 1828 map, but you can just make out “Cortlandt” or “Cortlandt’s” on the slender lane between Broadway and Elm Streets.

The part of Cortlandt Alley south of White Street, “was laid out separately and is 25 feet closer to Broadway,” according to the report. “Both parts of the alley were paved in the early 1820s.”

Cortlandt Alley almost extends four blocks—if you count one-block Benson Place, which lies just to the east on Franklin Street going south to Leonard Street.

A walk down Cortlandt Alley feels like entering a portal into a much earlier New York.

Nothing survives from the post-colonial city, unfortunately. This grimy lane with garbage bags on the sidewalks is lined with turn of the 20th century dry goods warehouses that feature enormous windows, elaborate fire escapes, and impressive shutters.

Bricked over windows and doorways face the alley, too, as well as old-school graffiti. No wonder Cortlandt Alley is so popular for film shoots.

A ping pong club has a door here, as does the Mmuseumm, the smallest museum in the city and located in a converted elevator shaft. Cortlandt Alley at White Street was once home to the 1970s-era Mudd Club.

“No dwelling house shall be erected thereon fronting on Cortlandt Alley,” a real estate article from The New York Times in 1859 read. That decree apparently changed, as luxury condos opened at number six.

A lot has changed in New York since the alley came into existence 202 years ago. But you can still imagine it as it was in the early 1800s: paved with stones, surrounded by new dwellings built on the landfill covering Collect Pond, and used as a shortcut by merchants, workers, servants, sailors, immigrants, and other New Yorkers in the 19th century city.

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13 Responses to “A walk down the longest true alley in Manhattan”

  1. A walk down the longest true alley in Manhattan | Real Estate Marketplace Says:

    […] Source: FS – NYC Real Estate A walk down the longest true alley in Manhattan […]

  2. A walk down the longest true alley in Manhattan | News for New Yorkers Says:

    […] Source: FS – NYC Real Estate A walk down the longest true alley in Manhattan […]

  3. Mykola (Mick) Dementiuk Says:

    In the 1970s it wasn’t as clean as your photos show it. Garbage, liquor bottles, beer cans etc covered the sidewalks. Besides that pot and drug sellers were in every doorway hallway. I didn’t like walking down that alley, I stuck to the bars on Canal St. Was more sociable.

  4. ephemeralnewyork Says:

    I will say when the weather warms up it stinks like urine, very old school NYC to me!

  5. Kenny Says:

    Mudd Club: wasn’t that the place where it was $10 to get in, then $10 to go to the 2nd floor then $10 more for the 3rd floor ?
    It should have been called the Pyramid Club.
    I never got off the ground.

  6. Steven Says:

    The wonderful podcast 99% Invisible ran a story about Cortlandt Alley a few months ago. The point of the story is that the Alley has been featured in many TV shows and movies, giving people the impression that New York is full of alleys.


    • ephemeralnewyork Says:

      This is fascinating, thanks for the link! If only NYC was actually full of cool old alleys….

  7. Ricky Says:

    The Pyramid Club opened in 1979 and is in the East Village on Avenue A. The Mudd Club operated from 1978 to 1983 in Tribeca on White Street,

  8. Gary Wright Says:

    The alley thing is what makes NY & Chicago feel so differently, IMHO. Appreciate learning a bit more about why we don’t see them as much here.

  9. petey Says:


  10. Что объединяет «Готэм» и «Смурфиков»? Их снимали в самом мрачном переулке Нью-Йорка! Рассказываем об этом месте — Киномания Says:

    […] начале Кортланд представлял собой мощеный проулок, окруженный новыми жилыми […]

  11. The Lower East Side’s Mechanics Alley is one of the last true alleys in Manhattan | Ephemeral New York Says:

    […] Theater Alley, beside Park Row near City Hall, was once home to Manhattan’s theater district. Three-block Cortlandt Alley makes for an evocative cut-through from Franklin Street to Canal […]

  12. Roosevelt Island Historical Society » Tuesday, July 19, 2022 – ALLEYS WERE A PRACTICAL WAY TO KEEP THE CITY CLUTTER FREE Says:

    […] Alley, beside Park Row near City Hall, was once home to Manhattan’s theater district. Three-block Cortlandt Alley makes for an evocative cut-through from Franklin Street to Canal […]

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