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.

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!


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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This article is pure gold. Easily ‘book level’ sophistication and completeness. Thank you.
Bloomingdale Reformed Church
WEA between 106 and 107
We have a winner.
I agree. According to Digital Culture of Metropolitan New York, it was taken circa 1905-1913.
Church of the Blessed Sacrament between Bway and Amsterdam Ave on West 71 St. There is church affiliated on W.70th Street.
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!
Looks like West End Avenue and Broadway by that park that had the rats, Straus Park.
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 –
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).
Fourth Universalist Church on Central Park West between 75th and 76th
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!)
The awnings were outlawed by NYC because they were considered a fire hazard on apartment buildings.
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.
You mean where Martin’s Wine shop sits? It’s hard to picture West End north of 106.
This is the old Harsenville Church, 949 WEA with the point of (what is now) Strauss Park in the foreground. c. 1910s
I believe the 10/21 mystery photo is just west of the corner of CPW and West 81st Street.
Thomas Palatucci
The new picture is the Bloomingdale Reformed Church, on West End between 106 and 107. 1906 to 1913. 949 West End, where I live!
synagogue on west 80-something beween columbus and amsterdam
The two buildings on either side are still there and look almost unchanged!
107th near bway. On north tip of straus park (titanic victims memorial) looking southwest. Idk when but that church isn’t there anymore.
Is this the Holy Cross Church on West 42nd?
Late 19th century?
If it’s a different church, it looks just like Holy Cross.
It’s Rodefh Shalom on W 83 St. Between CPW & Columbus Ave.
Riverside church answer to photo challenge 13