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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Tags: Alleys of Manhattan, Cortlandt Alley, Cortlandt family New Amsterdam, Exchange Alley NYC, hidden streets New York City, old alleys New York City