Friday Flashback #210

Over the years I’ve seen tons of photos of the Riverside Avenue/Wilton Road intersection, looking down and east from the Post Road hill.

But until I spotted this one — courtesy of Kathleen Kiska and Michael Tedesco — I’d never seen a view quite like this.

The wide, sharp shot — from 1914 — seems to capture turn-of-the-last-century Westport. A thriving business district existed right alongside residential neighborhoods. The little kid riding a bicycle looks straight out of Norman Rockwell.

But who was in charge of the roads? They look in even worse shape than they are today.

12 responses to “Friday Flashback #210

  1. That’s a wonderful picture. A treasure!

  2. I think parts of the Post Road, at that time period, were dirt, and not paved.

  3. i understand your point but the condition of the roads guaranteed slower and safer traffic. sounds good to me.

  4. Back then, these roads were not paved, merely dirt roads. I used to work with a gal whose mother was raised in Westport and she used to say she remembered when the Post Road was dirt when she was a girl.

  5. I knew they were dirt roads. I was making a joke!

  6. I can’t speak about 1914 directly, but if you read the Annual Town Reports from twenty years previous, you get at least a partial answer as to who was maintaining the roads: Town Residents. In the reports you will see payments to local people for repairing a section of road like “Charles Mills, repairs to North Avenue”.

  7. Sylvia Robinson Corrigan

    Imagine – 96 years ago, the busy intersection that we know today – so wide, so open, with just a lone young bicyclist enjoying the space!

  8. Wow great photo. Thanks!

  9. Wow! Like you Dan this is the first time I have seen a picture of the west side of the bridge without the Hunt and Downs building. That first house at the rivers edge where Fat Johns bar used to be would be pretty expensive real estate today! I can just see a Settlers & Traders sign there!

  10. Helen Avery Ranholm

    No be noticed the trolley tracks going down the middle of the road. My Dad told me many times about riding the Westport trolley.

  11. What a great photo. My only disappointment was clicking it for an enlarged version but nothing happened. I had to get right up to my screen to see that the lines in the roadway were actually trolley tracks. And a very different bridge existed then – a precursor to the steel grid that I remember as a child.

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