“Then & Now”: #28

This week, “Then & Now” curator and pre-demolition archivist Dave Matlow takes us from the western end of Westport, all the way to the east. The images are part of a project he worked on from 2004 to 2020.

A reminder: This is a community blog. Our neighbors live here. Some built those new structures; others are the second (or beyond) owners.

If you comment, please be kind. Taste is subjective. Wherever we live, everyone has loves their home.

Hermit Lane, November 2012 …

… and August 2026 (now called Stonewall Lane)

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Turkey Hill Circle, March 2009 …

… and August 2026.

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One house on Westfair Drive, September 2015 …

… and August 2026

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Also on Westfair Drive: October 2012 …

… and August 2026. (All photo/Dave Matlow)

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6 responses to ““Then & Now”: #28

  1. Scooter Swanson III

    Why, you ask about this transformation? As movie legend Stanley Kubrick once said: “Ask 100 questions and the answer to 99 of them is MONEY!” A resident of a newly constructed 25K square foot house was asked why he needed such a large domicile, he responded “because I can.” Herb Baldwin turning in his grave for the last thing he wanted was the town to be just for the rich.

    • You can’t explain it, you had to have lived it, and as each year goes by, less and less people will be alive to tell their memories. Remember when there was a fire in town , before radio dispatch and pagers, Westport used a siren to alert people where the fire was burning.

      • I do remember. I remember fires in which the Carousel toy store burned to the ground (twice); other fires devastated the furniture store downtown, the entire block of Post Road between Taylor Place and the entrance to the Taylor parking lot (opposite the downtown Starbucks), the Paint Bucket, the 200 wing of Long Lots, and your parents’ bowling alley.

        We have not had a fire like that in decades (knock wood). I’ll take our very professional Fire Department over volunteers summoned by sirens and pagers any day.

        • Dan, How about Party Lines whereby homes had shared local telephone lines. We shared a telephone line with two other families and each family had a unique ringing pattern. When the phone rang, you only answered it if it was your unique ring. Only one family could use the phone at one time. But things dramatically changed after 1958!

  2. Then and now is great! Documenting change by showing replacing a small house with a bigger house that is done to somebody else’s taste!!

    If only we could get rid of the first rate school system, the public Longshore golf and pools, Compo Beach and the other beaches, the diversity of good restaurants, the Westport Country playhouse, MOCA, the downtown shopping, the proximity to NYC etc etc- all the small houses “then” would still be here. And our house values would be half of what they are!

    It costs less to buy a house in Westport than to stay in NYC if you are sending 2 or 3 kids to private school!

    Just do the simple math.

  3. 60 years ago we had Compo Beach, Longshore, good schools, proximity to NYC, good restaurants (although I’m sure not as many) and homes whereby a fireman who had 4 kids and a wife who didn’t work could live in Westport on his fireman’s salary. We also had a lot more entertainment for the kids and adults. There was a movie theater, two separate miniature golf courses and two driving ranges and a bowling alley and batting cages for the kids to practice their swing. We had all this and the population was 8,000 less residents.

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