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.

An Avenue A artists enclave called Paradise Alley

Perhaps the name Paradise Alley was meant as a joke.

This little East Village enclave consisted of several small tenement buildings sharing a courtyard on the hard-luck corner of Avenue A and East 11th Street.

Or maybe Paradise Alley was a truly heavenly place to live and work, especially for the painters and writers who made it an unofficial arts colony through the 1960s.

However it ended up with its illustrious name, Paradise Alley has had a long history.

Built in the 1860s, the walk-up buildings here were home to the waves of German, Irish, and then Italian immigrants who settled in a neighborhood known by turns as Mackerelville, Kleindeutschland, and the northern end of the Lower East Side.

The Paradise Alley moniker supposedly came in the 1920s. By then, many artists and writers had moved in, renting rooms along with regular neighborhood folks for $17 to $25 per month.

That wasn’t small change for poor New Yorkers during the Depression. In January 1933, Paradise Alley residents went on a rent strike, insisting on a 25 percent reduction in rent and the mysterious demand of “proper sanitation facilities.”

The strike led to a wild anti-landlord and anti-police riot after the landlord evicted several tenants, all artists or writers, and left their belongings on the sidewalk.

Paradise Alley’s next claim to fame came thanks to Jack Kerouac, who fell in love with Beat poet Alene Lee, a Paradise Alley tenant in the 1950s.

Kerouac wrote a thinly veiled description of the enclave (and moved it to San Francisco) in his 1958 novel The Subterraneans.

Paradise Alley was “a big 20-family tenement of bay windows . . . the wash hung out in the afternoon the great symphony of Italian mothers, children, fathers . . . yelling from stepladders, smells, cats meowing, Mexicans, the music of all the radios . . .” as Kerouac described it.

In the 1960s, Paradise Alley was renovated; 40 families were relocated and rents raised to $80-$135 a month.

The builder hoped it would be a Patchin Place of the East Village. He put in a fountain, gas-lit lamps, and brickface facades. Morgan Freeman and composer David Amram were tenants.

The end came in a 1985 fire. Today, the corner hosts a senior living complex.

Could the 19th century tenement on the other side of the complex’s gate (top photo) be a last fragment of this lost East Village enclave?

Bedford+Bowery has a more in-depth piece from 2013 on Paradise Alley (with terrific photos).

[Second image: Avenue A looking north from 11th Street in 1933, NYC Municipal Archives; third image: Brooklyn Daily Eagle 1933; fifth image: a renovated Paradise Alley in 1962, New York Times]