It does seem like it was a more peaceful village way back when. Most of the new photos were taken on the morning of Oct. 21, 2021. I had wanted to take the shots before all the traffic started rumbling through; but unfortunately, I got the morning sun which didn’t make for the best pictures. I need to re-shoot a few of these. (For some, I stuck in clipped google streetviews as placeholders.) When not completely in the way, I did try to leave some cars in the pictures to “timestamp” what our world looks like today. 

You’ll find the streets in this order:

West Market St, East Market St., Mill St. (Rt.9 south of light), Montgomery St. (Rt.9 north of light), Chestnut St., South St., Livingston St., Spring Brook Ave., Others

West Market Street, 1912

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West Market Street, 1929

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East Market Street, 1908, 1916, and later

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Below, looking west, into town. c1900

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Below, looking east, near the Methodist Church.

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Below, 1952 view

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Below not exactly the right spot. I will need to re-shoot this one from further back after the leaves fall. The wooden building on the far right appears to still exist on the right side of the parking lot entrance. All the buildings between this and Schemmy’s are gone.

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Mill Street (Rt.9 south of light), 1900, 1913, 1920s

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Montgomery Street (Rt.9 north of light), 1907

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Montgomery Street, maybe late 1920's

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Montgomery Street, maybe 1940's

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Montgomery Street, c1910

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Montgomery Street, c1930

I got to this location by process of elimination. There’s only a few places this could be. Back in 1876 T.A. Van Steenburg had a large house, with a large lawn, now where Ruge Subaru stands. While the houses on Montgomery St. are not an exact fit, you can tell some of the buildings are newer than the card, so maybe this is the spot. This one is subject to updating.

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May 25, 1906 Kingston Daily Freeman, mentions automobile accident of John Jacob Astor on Montgomery St, Rhinebeck:


Chestnut Street, undated, pre-1930

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South Street, c1910, c1930, 1931

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Livingston Street, 1910, undated

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Academy Street, 1907

Livingston St., I understand from town historian Nancy Kelly, was once called Academy St. I still can’t find this location.

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Spring Brook Avenue, undated c1910

This is Rt.9 going out of town (north). Spring Brook Farm was across the street. It became the fairgrounds.

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Violet Avenue, undated

This is Mulberry St., looking north toward the fairgrounds. Chestnut St. crosses in front (in the old card). All you see in the photo from the exact location is trees and other newer houses, the marque house in the picture (41 Mulberry) is hidden from view. The new picture shows this house (with the red shutters) from a closer location. This card has to be old, c1900, as there are late 19th/early 20th century houses at the right two corner lots.

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This one I had to study for a while; I even had to ask Nancy Kelly if she knew. My best deduction is the house on right going out of town, 138 East Mkt St. (see below, next card is same house). It is definitely a winter scene, as you can’t get this shot from the right position in October. I’ll need to get a shoot of it in a few weeks when all the leaves are gone.

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Entrance to Rhinebeck from east (1925), west, north

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