Friday Flashback Follow-Up: Where The Hill Is It?

When I first saw last Friday’s flashback — a shot of an almost-empty Westport road, circa 1930 — I was pretty sure it was taken on State Street (now the Post Road), looking east past what is now Compo Shopping Center, toward where the Humane Society sits today.

But I wasn’t positive. So I asked readers what they thought.

Over 60 comments poured in. Many agreed with my guess. But others ranged up and down the Post Road, and across town to places like Nyala Farm.

Someone even thought I was right, but looking in the wrong direction (the old IHOP would be on the left, with the fire station and then — yes — the Humane Society on the right).

Alert “06880” reader Tom Ryan took out his camera. He offers these 3 images, and some thoughts.

This (above) was his original guess — the same as mine. However, he says, “you can’t see the road bend left (at the top) in the current photo. I think that rules it out.”

Picky, picky.

Here’s his second shot:

It shows Post Road West looking east, with Kings Highway Elementary School just out of the frame on the right.

Tom writes: “This one looks good as well. But notice the angle of the right side of the road. Seems dead straight in the original photo but more angled in today’s photo.”

Finally — looking east on Post Road West, just past Whole Foods — there’s this:

Tom says:

“I think this is a match, mostly because of the angle of the right side of the road in both past and current photos. You can also see the curve left in the distance, and the slope of the road seems to be the same.

“Lastly, the stone wall on the left is still there, and about the same distance from the road as in the original photo (although you can’t see it here because of the trees).”

The mystery continues. There’s only one thing we know for sure.

There was a lot less traffic back in 1930.

13 responses to “Friday Flashback Follow-Up: Where The Hill Is It?

  1. The old photo seems to be at an intersection. Note that tree near the car has been hit by cars and billboards are facing to side. Rte 1 was paved with concrete between 1906 and 1929 (I have knowledge of underground utilities on Rte 1). The old “Shore Road” (Rte 136) was an alternate to Rte 1. Much of this road was disturbed by I-95. This photo may have been taken at a section of road that is no longer there.

    • Bob Stalling

      Hi Dan.
      Good observations, though I may disagree about the tree being hit by a car (possibility of course)
      The tree appears to have a vase shape to it, which is a telltale growth habit of the American Elm, which was a common street tree back in the day. This tree may be dead as a result of Dutch Elm disease and the bark has peeled off as a result…
      Dutch Elm is spread by the Elm Bark Beetle and killed 77 million Elms between 1928 and 1989.

  2. Dan, this is impressive – some of your readers could find work as detectives for our police department!

  3. Also, do I see trolley tracks along the right edge of the road?

  4. Wendy Cusick

    On the last picture of Post Rd circa 2018… There’s wetlands behind those trees on the left hand side then a house and then Marion Rd. It’s too flat and wet.
    Also remember Post Rd was made wider and straighten a little back 70s.
    Post Rd (Westport Ave section) in Norwalk was done in 1975.
    I’m looking at the top two photos more closely.
    *This is my thoughts…additional visual I have in mind. Standing at Imperial Ave and Post Rd (in front of Parker Harding Funeral home) now visualize Post Rd (State St) to one lane up and down, looking East up the hill on the left where the large white church is on the hill (Saugatuck Congregation Church), Gas Station and Playhouse Square shopping. The stone wall is there and it has a hill. Take away the mature trees and add the billboards.
    *That 1930s picture to me is the crossroads of Post Rd (State St), Myrtle and Imperial Ave looking East.

  5. Wendy Cusick

    Zooming in this picture..πŸ”πŸ”πŸ•΅πŸ”ŽπŸ”ŽTrolley tracks sound like a possibility. However, the trolley tracks I believe were always embedded in red brick. The Trolley Barn on Wall St (now a restaurant) had the tracks in the red brick. When they have to pull up the road to fix utilities or something. The red brick and trolley tracks are visible.
    Possibly those tracks were used to make it easier pull heavy loads up hills??
    πŸ•΅ πŸ•΅ πŸ•΅ πŸ•΅ (detective hat on πŸ˜‰)

  6. Fred Cantor

    Tom, great stuff. (And I’m not just saying it because your photos seem to support my gut take on this.) I thought the stone wall could be something still present and perhaps helpful in trying to figure this out.

    If someone were able to get better resolution on the small billboard in the background that appears to say β€œWelcome to Westport,” I think that would clinch it. (Just kidding.)

  7. Wendy Cusick
    This might be of interest to everyone.
    Aerial Photography πŸ“· πŸ“· πŸ“· πŸšπŸ›©πŸšπŸ›©πŸš

  8. Wendy Cusick

    Hmmm πŸ€”πŸ€”πŸ€”
    Just went onto Google street view finger ‘driving’ (scrolling) up Post Rd (State St Google still calls it State St😏)
    I stop at the intersection of East Main St and The Mews looking East toward the Human Society (looking up hill next door gas station, medical building, old Steinway piano and then Fire Department Headquarters). Visualize making Post Rd (State St) narrowier, Telephone Utility Poles on right hand side, road bends to the left.
    *I think your readers from past post and current are correct with Humane Society hill.

  9. Michael Calise

    Do not know if there was a connection but the billboard with the oil filter ad might have been for a gas station on the left just over the hill exactly where the Fire Station is now located. My Dad would stop there often. it was a frame building (house) with a front canopy and one or two gas pumps. I remember glass jars lined up at the front door filled with motor oil ready for sale. The owner had a peg leg and lived in the house with his family. I remember him as a very engaging individual. This was after the war 1946-50

  10. Peter Barlow

    I agree with Tom that his third view is the updated location. The original view, I believe, is the Post Road west of Marion Road near the Westport-Norwalk line looking east. I remember the trolleys some years later.

  11. Seth Van Beever

    Westport …A Special Place mentions taking a trolley trip to Norwalk, whitch would account for the tracks near Marion Rd.
    Anyone know what the “J” marker in front of the car is? Or is it just a barricade for a culvert to a tributary that runs under the road?