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Upper West Side Historical Photo Challenge No. 28

June 2, 2026 | 8:19 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 Historical Photo Challenge #27
Subject:  Rip’s Tennis Courts
Location: West End Ave between West 94th and 96th streets
Year: approximately 1917
Image Source: Museum of the City of New York
Clues: The Hudson River view tells you that we’re looking south, and the distance to the river dictates that this is West End Avenue rather than Riverside Drive or Broadway.  At least two of the buildings from 1917 are standing today, including 749 WEA, a handsome 1912 Rouse and Goldstone-designed apartment house featuring a top story arcade described by LandmarkWest! as having “engaged columns, decorative piers and shields and cartouches.”  Further down WEA, the second building visible behind the courts is 306-308 West 94th, a George Pelham apartment house from the turn of the 20th century that has been rentals, SROs, and the Hotel Alexander.

Top: West End Avenue looking south toward 96th Street around 1917. Insets: Still-standing apartment buildings.  Bottom: Contemporary aerial photograph with location of Rip’s Tennis Courts highlighted by dashed white line.

The rest of the story: Robert “Rip” Dolman was a legend on the Manhattan tennis scene of the first half of the 20th century.  His commercial tennis ventures, operated with three brothers, contrasted with the snootier tennis clubs, building courts on vacant land being held for appreciation before development. Their first location was this one on West End Avenue—note the chain link fence and the homemade-looking sign. Photographs taken during the Hudson-Fulton Celebration show that there were tennis courts at West 96th Street at least as early as September 1909.  In winter it was easy to flood the courts and turn them into an ice-skating emporium.  It looks like a humble operation, but the Dolman tennis empire, which at various times included courts at 39th and Park and at Sutton Place, attracted some of the best players of the era—Bill Tilden, Don Budge, and Brooke Shields’s grandfather Frank Shields.

Top: Rip’s Tennis Courts in 1935. Bottom: The courts in 1909.  Note crowds on the rooftops watching passing ships during the Hudson-Fulton Celebration.  Center right: Advertisement for Rip’s.

…and that’s the story behind the mystery image.  Scroll back to the top of the column and take on your next challenge, Sherlockians!  If you’ve missed any pictures in this series, you can find the complete set on my author page.  All photos used with 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.

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11 Comments
Elgin93
Elgin93
20 days ago

This seems to depict the construction of the General Grant Houses and the erasure of the West end of West 124th Street. the tall building on the far right is 1320 Amsterdam Avenue. The middle of the frame shows a remnant of the intersection of Amsterdam Ave. and West 124th Street (now Erased) — Note the large outcrop of rock to the far left below the middle of the shot– This is still there today on West 123rd Street with the Margaret Douglas School perched on top of it. You can see the slope of Amsterdam Avenue as it dips from left to right towards the bottom at what is now 125th Street off frame to the right. (we are looking SW). Note how the buildings in the top left of the frame step up as they go South. These are still there on Amsterdam between 123 and 122nd Streets.
This would be around 1954-5

6
Reply
Anonymous
Anonymous
20 days ago

Love these! Thank you!

0
Reply
Steven
Steven
20 days ago

Looks like Amsterdam Avenue from 121st street or so to 125th.

Last edited 20 days ago by Steven
0
Reply
Anne-Marie Diamond
Anne-Marie Diamond
20 days ago

Photo#28: 100 Street between Amsterdam & Columbus circa: 1953-1958?

0
Reply
NYCNAT
NYCNAT
20 days ago

1950s deconstruction of smaller tenant buildings and construction of the Grant Houses and Morningside Gardens?

1
Reply
Tim
Tim
20 days ago

Manhatanville taking all the beautiful townhouses and buildings down to build the Manhattanville and Grant Houses.

1
Reply
Sean Berserker
Sean Berserker
20 days ago

125th and Amsterdam Avenue

0
Reply
Sam
Sam
19 days ago

Blocks and blocks of beautiful townhouses and brownstones were removed to build the Grant and Manhattanville Houses. I wonder if anyone knows this.

0
Reply
Postal Patron
Postal Patron
19 days ago

Frederick Douglas Houses

0
Reply
Dennis
Dennis
18 days ago

This is Amsterdam Avenue from 122nd Street to LaSallle Street. The upper middle portion (from 123rd Street to LaSalle Street) is now Morningside Gardens which was constructed in the mid 1950s. Grant Houses were constructed on the opposite side of Amsterdam. If you look real hard, on the left side of the photo slightly above the middle, there is a rock formation, and you can make out the three sided “fort” that was constructed as a defense against a possible British invasion in 1812. The rock formation, including the fort, were blown up in the mid 1960s and a school was built on the site. (Footnote: One street south of the photo, 121nd and Amsterdam ,is where George Carlin grew up.)

2
Reply
M L
M L
17 days ago

Amsterdam and LaSalle! Wow, what a throwback.

0
Reply

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