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    Upper West Side Historical Photo Challenge No. 25

    April 21, 2026 | 8:45 AM
    in COLUMNS, HISTORY, NEWS
    11

    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 #24
    Subject:  Leake and Watts Orphanage, now called the Ithiel Town Building
    Location: Amsterdam Avenue, between West 110th and 111th Streets
    Year: approximately 1895
    Image Source: Cathedral of St. John the Divine Archive
    Clues: Identifying this image is as simple as recognizing the large Greek Revival building, but that building’s prominence has diminished considerably since it was built almost 200 years ago, and many UWSers don’t realize that a major structure designed by one of America’s earliest native-born architects still stands—well, part of it, anyway—in Morningside Heights.  One wing of the building was removed, and the remainder is now dwarfed by the Cathedral of St. John the Divine.  The cathedral is so close to the former orphanage that the perspective in our challenge photo–showing the backside of the orphanage looking south from a vantage point in the cathedral’s transept during construction—is no longer available.

    Top: Leake and Watts Orphanage around 1895, photographed looking southeast from the construction site of St. John the Divine. Note the 9th Avenue El, heading east along 110th Street before turning uptown.  Bottom: the view today, as reconstructed by Google Earth but looking north instead of south. The eastern wing of the former orphanage is missing.

    The rest of the story: There is a lot going on in this rich image.  The Leake and Watts orphanage opened in the 1840s—it’s probably the oldest extant structure in Morningside Heights.  The orphanage moved to Yonkers after the Episcopal Church bought the land for the cathedral in the late 1880s.  One of the orphanage building’s two symmetrical wings was removed in 1950, purportedly to allow more space on the crowded campus—the Close.  Ithiel Town, after whom the building is now named, was a person and not a place!  He designed Federal Hall downtown, among many significant buildings and bridges.  You might also have noticed the elevated railroad—this was the 9th Avenue El, which stood until 1940 and made two sharp curves at 110th Street, where it was the highest point in NYC’s rapid transit system.  If you look closely at the train that is passing in the photograph, you’ll notice that it’s pulled by a locomotive—this was a steam train, not an electrified system.  And the very sharpest of Rag readers may have caught the distinctive trapezoidal shape of the Lion Brewery.

    Top right: early drawing of Leake & Watts showing its eastern wing with balconies.  Middle: Ithiel Towns’s Leake and Watts building around 1895 with the 9th Avenue El in the background.  Bottom: the El at 110th Street.

    Shoutout to readers: Most commenters recognized this building, which still (partly) stands in the shadow of St. John the Divine.  Glen asked what the shadowy rectangle in the upper right corner was.  I dunno.  It would be somewhere between West 100th and 105th Streets, I’d estimate, probably between Columbus and Broadway or perhaps on Broadway.  The Church of the Holy Name of Jesus on West 96th Street had a tower that lacked a steeple until 1918, but I don’t think the tower would have stood out as much as this structure did.  Anyone have a theory?


    …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 columns in this series, here is the complete collection. All photos used by permission.

    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.

    Subscribe to West Side Rag’s FREE email newsletter here. And you can Support the Rag here.

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    11 Comments
    Paul
    Paul
    5 months ago

    There was a Manhattan Chess Club in the Henry Hudson Hotel, I believe the location is the site of the newer hospital formerly called Roosevelt.

    Played there in the mid 60s.

    0
    Reply
    Anne Reingold
    Anne Reingold
    5 months ago

    Chess place 96th and Broadway

    0
    Reply
    Merrick Dean
    Merrick Dean
    5 months ago

    There was a chess club and/or bridge club in the 70s . Looks like that ? My brother in law and sister played but not i 😉

    0
    Reply
    Larry
    Larry
    5 months ago

    Yeshiva Ketana at 346 w 89th St.

    1
    Reply
    Paul Bleifeld
    Paul Bleifeld
    5 months ago

    Chess Club–West 72nd St. at Broadway

    1
    Reply
    ecm
    ecm
    5 months ago
    Reply to  Paul Bleifeld

    You mean in the old Colonial Club formerly on the SW corner? That was my first thought just from the look of the room, but I was unable to find supporting evidence. A definite maybe.
    Another possibility that crossed my mind, to similar nonresult, was the building at 2307 Broadway — the former West Side R******** Club, where Ivy League chess tournaments used to be held.
    In short, I don’t know.

    0
    Reply
    marjorie g
    marjorie g
    5 months ago

    former chess club in the ansonia?!

    0
    Reply
    Elgin93
    Elgin93
    5 months ago

    170 Riverside Drive (today Yeshiva Ketana of Manhattan.

    0
    Reply
    JjjjL
    JjjjL
    5 months ago

    Small correction regarding Leake and Watts — location is between 111th and 112th (not 110th and111th). The cathedral building centers on 112th…

    0
    Reply
    Bob Roistacher
    Bob Roistacher
    5 months ago

    Chess club at 210 West 72nd street. Thank you, Gemini je

    0
    Reply
    ecm
    ecm
    5 months ago
    Reply to  Bob Roistacher

    I believe 210 is a tad too far west to have been the Colonial Club, but is that the building you had in mind? Does Gemini je (?) offer any supporting evidence? The Colonial Club was my first theory, based on the room’s “look’n’feel”, but I was unable to find corroboration.

    0
    Reply

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