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Upper West Side Historical Photo Challenge No. 12

October 21, 2025 | 8:20 AM
in COLUMNS, HISTORY, NEWS
23

By Rob Garber for the Bloomingdale Neighborhood History Group

Welcome to another installment in the Rag’s Historical Photo Challenge. The image above was taken somewhere on the Upper West Side, sometime in the past. Can you figure out where, when, and what it shows? Look closely; this week’s challenge photo, like the others in the series, includes clues that will help you identify the scene, if you’re a dedicated UWS history sleuth. And even if you don’t recognize the picture—not to worry! Come back in two weeks and I’ll decode it, show you the clues that help identify it, and—best of all—tell you a story the image unlocks, because this column isn’t just a test of your neighborhood knowledge; it’s also a rolling celebration of the people, buildings and events that wove the tapestry of the Upper West Side.

Ready? If you think you know where and when the photo was taken and what it shows, post your answer as a comment on this column.


Solution to Photo Challenge #11

Subject: The roof of the underground boiler room of the Dakota
Location: 15 West 72nd Street
Dates: 1927, 1924 and 1880s
Image Sources: Hamilton Aerial Map of Manhattan (1927), New York City Municipal Archives (1924) and Office of Metropolitan History.

Clues: I promised you that every photo challenge would include one or more clues to its identity.  This may have been one of the most difficult—there were three photos, but the clues were sparse.  The shadow cast by the ornate roof outline of the Dakota was a clue—is there any other UWS building with such a jagged profile?  And the surprisingly plain west-facing façade of the Dakota is still there, hiding in plain sight but often overlooked because of the exuberant ornamentation of the other three sides.

Top: The sharpest aerial view of the Dakota and the roof of its adjacent boiler room roof, taken in 1927.  The photo challenge image is outlined with white dashes.  Second from top: The relationship between the shape of the shadow in the mystery photo and the roofline of the Dakota’s western façade.  Second from bottom: A unique street-level photo of the boiler room roof, looking east toward the unadorned west side of the Dakota in the late 1880s or 1890s.  Bottom: The Dakota’s western façade today, showing unchanged window positions.

The Rest of the Story: The Dakota has loomed large in the collective imagination of the Upper West Side ever since it was built more than 140 years ago.  Uber-luxurious and colossal in every way (Real Estate Record and Guide noted in April 1884 that its 56 apartment suites and 500 rooms would be home to 3,000 people (!), “including the army of servants and other auxiliaries.”   At the time of its construction, electrical service in New York City was limited to a small part of lower Manhattan–so an independent underground power plant was built on vacant land next door to the Dakota by its developer to provide heat and lighting to the new building as well as to a row of buildings that was also owned by the Clark family on the north side of West 73rd Street.  The unattractive roof was concealed by fences and hedges, and rarely appears in images, in contrast to the photogenic Dakota. The electrical grid reached the Upper West Side in the 1890s and the Dakota’s private power plant became unnecessary.  Through the first half of the 20th century, the property was retained by the Clark family and apparently was at times a garden and a tennis court used by the Dakota’s occupants.  By the early 1960s it had suffered the indignity of being converted into a parking lot.  Eventually the valuable real estate was developed into Mayfair Towers, an apartment building completed in 1964.  If any West Side Rag reader knows of photographs documenting the use of the land just west of the Dakota as a tennis court or garden, please share them—surely someone pointed a camera out their Hudson River-facing Dakota window between 1900 and 1960!

Top: An extraordinary photograph taken from the new Dakota looking west in the 1880s, showing the block between Central Park West and the Ninth Avenue El filled with rubble and some of the original terrain of the island.  Middle: View NW from Central Park West, showing the southern façade of the brand-new Dakota and a glimpse west of the building with boulders and in the distance, some of the Clark-owned row houses on the north side of West 73rd Street.  Bottom: Photograph from the 1890s when the Dakota’s power plant was hidden by fences and hedges.
Top: Fire insurance maps from 1885 (left) and 1955 (right), showing the persistence of the power plant or “boiler room”.  Note that in 1955, the land west of The Dakota was also used as parking.  Bottom: The inglorious parking lot years—1950s or early 1960s.

Shoutout to Readers: this was a tough one, but William Hennessey nailed it.


…and that’s the story behind the mystery image.  Now scroll back to the top of the column and take on your next challenge, Sherlockians!  If you’ve missed any pictures in this series, here is the complete collection.

About the author:  Rob Garber has lived on the Upper West Side since the late 20th century and is a member of the Bloomingdale Neighborhood History Group.  To learn more, visit their website at upperwestsidehistory.org.  All photos in Upper West Side Historical Photo Challenge are used by permission.

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23 Comments
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Good Humor
Good Humor
27 days ago

This article is pure gold. Easily ‘book level’ sophistication and completeness. Thank you.

7
Reply
drg
drg
27 days ago

Bloomingdale Reformed Church
WEA between 106 and 107

4
Reply
Maryjane
Maryjane
26 days ago
Reply to  drg

We have a winner.

2
Reply
Ruth
Ruth
27 days ago
Reply to  drg

I agree. According to Digital Culture of Metropolitan New York, it was taken circa 1905-1913.

0
Reply
Ann Winton
Ann Winton
27 days ago

Church of the Blessed Sacrament between Bway and Amsterdam Ave on West 71 St. There is church affiliated on W.70th Street.

2
Reply
Steve M
Steve M
27 days ago
Reply to  Ann Winton

That’s what I thought at first, too but then I looked at the street in the foreground and it didn’t match up. Looks very similar, though!

0
Reply
Sal Bando
Sal Bando
27 days ago

Looks like West End Avenue and Broadway by that park that had the rats, Straus Park.

1
Reply
Bloomingdaler
Bloomingdaler
27 days ago

That’s the Bloomingdale Reformed Church in its last incarnation, on West End Ave between West 106 and 107. It was only there for seven years. Founded in 1805, it was one of the oldest congregations on the Upper West Side (Harsenville before that), th is building stood between 1908 and 1913. That’s Bloomingdale Square (now Straus Park) across the street.
– Anthony Bellov –

0
Reply
James
James
27 days ago

This is upper end of West End Ave. between 106-107th streets.. A triangular space …later named Strauss Park,…is immediately outside the frame to the left of image (east).

1
Reply
Jessica
Jessica
27 days ago

Fourth Universalist Church on Central Park West between 75th and 76th

0
Reply
Lizzie
Lizzie
27 days ago

What’s notable is the awnings on the windows. These were once commonly used keep the sun out of interiors in the pre-AC era. You’d see them on grand Victorians in Brooklyn and tenements on the Lower East Side. I remember them on my grandparents’ house in Pennsylvania in the 1960s. They really helped keep interiors cooler!

(The girls with their parasols…same idea!)

2
Reply
Paul
Paul
27 days ago
Reply to  Lizzie

The awnings were outlawed by NYC because they were considered a fire hazard on apartment buildings.

0
Reply
ACH
ACH
27 days ago

The photo is on West End Avenue facing west, between 107 & 108 Street. Strauss Park is at the southern end. The water trough was removed to provide metal for the war effort.

0
Reply
Anthony
Anthony
27 days ago
Reply to  ACH

You mean where Martin’s Wine shop sits? It’s hard to picture West End north of 106.

0
Reply
Elgin93
Elgin93
27 days ago

This is the old Harsenville Church, 949 WEA with the point of (what is now) Strauss Park in the foreground. c. 1910s

0
Reply
Thomas Palatuuci
Thomas Palatuuci
27 days ago

I believe the 10/21 mystery photo is just west of the corner of CPW and West 81st Street.

Thomas Palatucci

0
Reply
Brian
Brian
27 days ago

The new picture is the Bloomingdale Reformed Church, on West End between 106 and 107. 1906 to 1913. 949 West End, where I live!

0
Reply
i'm thinking. Columbus Avenue & West 97th Street
i'm thinking. Columbus Avenue & West 97th Street
27 days ago

synagogue on west 80-something beween columbus and amsterdam

1
Reply
Flaky cheese danish
Flaky cheese danish
27 days ago

The two buildings on either side are still there and look almost unchanged!

0
Reply
Robert fried
Robert fried
27 days ago

107th near bway. On north tip of straus park (titanic victims memorial) looking southwest. Idk when but that church isn’t there anymore.

0
Reply
Robin Block
Robin Block
26 days ago

Is this the Holy Cross Church on West 42nd?
Late 19th century?
If it’s a different church, it looks just like Holy Cross.

0
Reply
Donald Sussis
Donald Sussis
23 days ago

It’s Rodefh Shalom on W 83 St. Between CPW & Columbus Ave.

0
Reply
Howard moi
Howard moi
23 days ago

Riverside church answer to photo challenge 13

0
Reply

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