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    Upper West Side Historical Photo Challenge No. 7

    August 12, 2025 | 8:31 AM - Updated on August 24, 2025 | 8:34 PM
    in COLUMNS, HISTORY, NEWS
    37

    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 Historical Photo Challenge #6

    Subject: Early protest against the Vietnam War
    Location: West 111th Street between Broadway and Riverside Drive
    Date: November 13, 1965
    Image Source: New York City Municipal Archives

    Clues: The Caravan Restaurant on the corner looks a lot like Tom’s before it was Tom’s, doesn’t it—so the NE corner of Broadway and 112th, yes?  Close, but no—the Caravan was a block away, in the spot now occupied by Famiglia Pizza on the SW corner of Broadway and 111th.  This crowd was gathered on a rainy November day—but for what?  It doesn’t look like the West 111th Street Association’s annual block party.

    Top and bottom left: antiwar rally on West 111th St in November 1965.  Top and bottom right: same locations today.

     

    The rest of the story: Even more interesting than the location is the question—what was going on here?  Why was there a crowd and mounted police on a quiet  side street?  The answer is that it was an early protest against the war in Vietnam.  These photos are stills from film footage shot by a surveillance team from the New York City Police Department.  Throughout the 1960s, the NYPD recorded numerous events—mostly civil rights or antiwar marches, but also counterprotests, visits to New York by presidents, even the Gemini 3 astronauts’ parade.

    The rally on West 111th Street featured speakers from the Students for a Democratic Society, the W.E.B. DuBois Club, and the Progressive Labor Party.  It attracted 600 protesters, counterprotesters, onlookers, journalists, and 40 police.  The New York Times reported that counterprotesters were “herded” behind police barricades across Broadway. The Columbia Spectator’s coverage of the event noted that some speakers claimed there were FBI photographers in the crowd—there certainly were lots of guys with cameras.

    Top: antiwar rally on West 111th Street and the Columbia Spectator headline. Bottom: counterprotesters across Broadway and the New York Times headline.

    Shoutout to readers: Many thanks to all you WSR readers who love the history of your community enough to engage and debate. This was a toughie. The Caravan Restaurant was quite real—it wasn’t part of a movie set. The SW corner of Broadway and West 111th has hosted a series of restaurants over the decades, and in the early 1960s, it was the Caravan.

    Top: 1962 ad for the Caravan Restaurant.  Middle: Caravan Restaurant in 1965. Bottom: SW corner of Broadway and West 111th St today.

    …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.

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

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    Please limit comments to 150 words and keep them civil and relevant to the article at hand. Comments are closed after six days. Our primary goal is to create a safe and respectful space where a broad spectrum of voices can be heard. We welcome diverse viewpoints and encourage readers to engage critically with one another’s ideas, but never at the expense of civility. Disagreement is expected—even encouraged—but it must be expressed with care and consideration. Comments that take cheap shots, escalate conflict, or veer into ideological warfare detract from the constructive spirit we aim to cultivate. A detailed statement on comments and WSR policy can be read here.

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    37 Comments
    Ginger
    Ginger
    1 year ago

    Looks like the man in foreground is giving tennis lessons. Below 79th Street on Riverside Drive in the 1920s?

    0
    Reply
    Steve_UWS
    Steve_UWS
    1 year ago
    Reply to  Ginger

    Was going to say Riverside at 74th. Prepared to be wrong.

    0
    Reply
    Ish Kabibble
    Ish Kabibble
    1 year ago

    Westside Tennis Club?

    0
    Reply
    Lisi
    Lisi
    1 year ago

    Agree with Riverside Park in the 70s. Perhaps where the basketball courts are now?

    0
    Reply
    Amelia
    Amelia
    1 year ago

    The tapestry of the Upper West Side. Who new I was a stitch in a tapestry!

    1
    Reply
    Harriet
    Harriet
    1 year ago

    West Side Tennis Club – CPW 89th St

    1
    Reply
    Lll
    Lll
    1 year ago
    Reply to  Harriet

    No. Freaking way. And there was Claremont Rusng Academy o, probsy called something else then, on 89th and Columbus

    0
    Reply
    Steven
    Steven
    1 year ago
    Reply to  Harriet

    This is correct. Here’s the street view of the buildings on the north side of 89th today. Matches the buildings in the photo. https://maps.app.goo.gl/858J2mvrLBHdaiiW9

    0
    Reply
    Ginger
    Ginger
    1 year ago
    Reply to  Steven

    I agree. 89th/CPW and not Riverside Drive, though the below -street level courts looked like they “belonged” off RSD! Thanks for picture. That 291 CPW building with the striped facade is, I believe, a Clarence True building. He was a prolific architect on the UWS in the 1890s and also created many Riverside Drive row houses. (#s 74 – 77 and 81 – 89). Makes a good walking tour, all below 81st St.

    0
    Reply
    Life-long Upper West Sider
    Life-long Upper West Sider
    1 year ago
    Reply to  Steven

    Is this Steve Harmon who confirmed the location? Or is it wishful thinking because Throwback Thursdays have come to an end (or maybe just a pause??A girl can hope)

    0
    Reply
    Steven
    Steven
    1 year ago
    Reply to  Life-long Upper West Sider

    No, different Steven

    0
    Reply
    i'm thinking. Columbus Avenue & West 97th Street
    i'm thinking. Columbus Avenue & West 97th Street
    1 year ago

    i’m thinking it is Columbus Avenue and West 97th Street

    0
    Reply
    Billy Bob
    Billy Bob
    1 year ago

    The tennis courts of The Dakota

    1
    Reply
    Laura
    Laura
    1 year ago

    These are really hard!

    I remember that Drago show repair very well, except – am I crazy, or did it used to be a little bit farther down the block, closer to 110th St? Is it possible it moved a few doors down at some point? It was there (on that block) until at least the 90s, maybe even later than that. It was an amazing place, they were so good.

    1
    Reply
    Carnevale Cantorum
    Carnevale Cantorum
    1 year ago
    Reply to  Laura

    Wasn’t there also a Drago shoe repair between 86th & 85th and Broadway, in a space that now has another shoe repair shop? Next to Broadway Chemists.

    1
    Reply
    Elgin93
    Elgin93
    1 year ago

    There were once tennis courts at Amsterdam between 92nd and 93rd, I believe, but these are not them. This would be the Tennis courts on 96th Street and West End Ave, where now stands P.S. 75.
    Photo & clothing feels like 1910?

    1
    Reply
    Coco
    Coco
    1 year ago

    I think this might be the tennis courts that spanned 98-99th street on Columbus ave.

    0
    Reply
    Mark
    Mark
    1 year ago

    re: Challenge #6 – Why was that location chosen for the anti-war rally? Proximity to Columbia U?

    1
    Reply
    Janet
    Janet
    1 year ago

    I agree with the West Side Tennis Club but I think it was 88th and CPW in the 1890s. Later it moved up near Columbia before finally going to Forest Hills.

    0
    Reply
    Jesse Margolis
    Jesse Margolis
    1 year ago

    We’re looking at the tennis club that was replaced by the St. Urban on West 89th St and CPW. I happened to walk by the St. Urban yesterday and look at the sign on the building, which says it was built in 1906 and replaced a tennis club. On the north side of West 89th Street, you can see the 291 CPW (which houses part of the Dwight School) and a row of brownstones that still stands.

    3
    Reply
    Rochelle Perlman
    Rochelle Perlman
    1 year ago

    This is the Tennis Courts that were on the Eastside of Columbus Ave. They were part of the Park West Village development. That part of the block is now home to major retailers like Home Goods and a tall apartment building.

    0
    Reply
    Sid
    Sid
    1 year ago

    Courts on 84th and Amsterdam?

    2
    Reply
    Joan Nilson
    Joan Nilson
    1 year ago

    Is it the old Tennis Court at Columbia University on 120th street between Broadway and Amsterdam?? It was torn down in the mid-late 1950s for another building

    1
    Reply
    Robyn Roth-Moise
    Robyn Roth-Moise
    1 year ago

    Tennis behind the Dakota building

    0
    Reply
    Ken J.
    Ken J.
    1 year ago

    The tennis games being played was a tournament because those two men (one in chair, the other standing) are officiating.

    0
    Reply
    AnnieNYC
    AnnieNYC
    1 year ago

    89th Street between CPW and Columbus? The row of buildings to the right look the same as now.

    0
    Reply
    Grayson
    Grayson
    1 year ago

    These photo challenges are great, thank you 🙂

    2
    Reply
    Steve
    Steve
    1 year ago

    This is the old Westside Tennis Club at CPW and West 89th Street, before the
    club moved to Forest Hills. Now it’s the St. Urban apartment house at 285 CPW.

    0
    Reply
    Allie
    Allie
    1 year ago

    According to an old NYT article, this is the The West Side Tennis Club at Central Park West and 89th Street in 1900. But some other research suggests that it was actually called the New York Lawn Tennis Club at that time (and only became connected with the West Side Tennis Club when it moved to Forest Hills).

    0
    Reply
    Marcel Sislowitz
    Marcel Sislowitz
    1 year ago

    There were tennis courts on West End Avenue at the location of the present day PS 75 bet 95-96. They were flooded in the winter for ice skating. Not sure if that’s correct but my guess

    0
    Reply
    Kurt
    Kurt
    1 year ago

    Columbia University tennis courts at 114th St and Broadway (the southeast corner of the campus). Carmen and Ferris Booth Halls were eventually built on the site, the latter eventually replaced by Lerner Hall.

    0
    Reply
    Kurt
    Kurt
    1 year ago

    Based on the clothes I would say that this is from the 1920s or 1930s.

    0
    Reply
    Steevie
    Steevie
    1 year ago
    Reply to  Kurt

    Kurt: Look at the row of benches. Do you see the woman all in black? Way before 1920s.

    2
    Reply
    30 years here
    30 years here
    1 year ago
    Reply to  Steevie

    I’m with Steevie; there are 2 women with shoe-length skirts: one in white at the top of the stoop to the far left, one in black sitting on a bench observing a back-row court. By the 20s, skirts were shorter (cue: “Anything Goes”) So I’d guess the first decade of the 20th century. But I am confused by the person on the left front court, with a femme-ish shape but wearing pants.

    The lack of slope in the block of brownstones leads me to think this can’t be 96th and West End; that’s a noticeable hill. So I’m leaning toward the second location of the West Side Lawn Tennis Club, 117th & Amsterdam, which they had from 1902-1908.

    0
    Reply
    Tim
    Tim
    1 year ago

    Looks like Columbia University campus courts.

    0
    Reply
    Steven Kunreuther
    Steven Kunreuther
    1 year ago

    I’ve been on and off the board at 285 Central Park West for many years. A while ago, we decided to put a plaque up on the building which is still there. I insisted that they include the following sentence in the description of the building. “Prior to the construction of the building, this site was the first home of the West side tennis club.”. I never saw an actual picture of people playing on the court and I’m so glad you put this together. If you would like to see the plaque, please send me an email address and I will forward it to you.

    3
    Reply
    DonB
    DonB
    1 year ago

    One of the nice parts of UWS life is how you can see scenes today that haven’t changed much for a century or more. I’m not referring to below street grade tennis tournaments, but to the brownstones and the distinctive apartment building on West 89th St close to Central Park West. The Google street-view today shows a strong match with the challenge photo.
    But then there are those tennis courts on the south side of the street, where today several substantial looking buildings stand. This turns out to be the key to dating the photo. The brownstone buildings on the north side of 89th St. were built in 1900 according to the NYC bulding department web site. The building on the south side, where the tennis courts are, was built in 1905. So my guess is 1903.

    0
    Reply

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