Friday Flashback #12

As downtown prepares for its Next Big Thing — Bedford Square, opening in the spring, will change completely the way we drive, walk and imagine the entire area — let’s look back on a previous version of Main Street.


Fred Cantor found this in the 1964 Staples High School yearbook.

It’s fascinating for several reasons. It shows:

  • The original location of Oscar’s
  • The old Mobil station (now Vineyard Vines)
  • Two-way traffic all the way to the Post Road.

A lot has changed in 52 years.

Then again, a lot hasn’t.

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32 responses to “Friday Flashback #12

  1. Wow– that is a flashback..

  2. Great shot! Much cleaner sight lines on Main Street these days without the bulky telephone poles

  3. My family moved to Westport in the early 50’s. My mother shopped downtown for meat and fish and I hung out with my friends at the Y and went to the movies. That’s all gone now. I don’t know anyone who goes downtown anymore, unless they have to.
    What a shame we haven’t done better in all that time. How about closing that stretch between post road and Elm Street to cars and bring in the farmers market, restaurant seating, arts and craft kiosks? Anything would be better than what we have now, in my opinion.
    Tenants are struggling due to decreased foot traffic stores are closing every day. The Y used to bring hundreds of people downtown organically and now we have lost that traffic. Our “shopping mall” is poorly conceived, boring and way behind the times. Our zoning boards are still stuck in the pre-Internet 80’s. With Bedford Sq coming wouldn’t it be a great time to reinvent Main Street?

    • x Jeff Giannone

      My grandmother — an immigrant from Berlin who was elderly by then — even went to the ‘German Club’ at the Y. She was always making new elderly German speaking friends through this club — who would then come to our house on Sundays for coffee&cake. That Y served such varied & important purposes to people then. Part of me wants to fly into this photo & find her there.

    • Michael Calise

      I take issue with your remarks Jeff. The members of the Planning & Zoning Commission and the Zoning Board of Appeals are hard working, dedicated individuals who contribute greatly to our town in highly pressured positions.
      We are fortunate to have their willingness to serve

      • Jeff Giannone

        Sorry to offend you Michael. I’m sure the volunteers have done their best but in my opinion over the years they have also been slow to adopt changes that we all now enjoy. I’m thinking about the 1500′ liquor license, the restaurant outdoor seating, the setbacks and mixed use regs, the list goes on. I just believe that downtown is essentially dead. There is no life to it and that’s a real shame. Maybe zoning is not to blame, maybe it’s all of us. Thanks

  4. I was three when this was taken. Am I the only person who searched for their family car in this photo?

  5. Awww I love seeing the old hometown! I did look for our family car! It’s wonderful to see these old pictures…thank you. I loved shopping downtown at the local stores…happy westport memories!

  6. I liked it better the way it was…Last time I visited in Westport, all the places I loved were gone except Oscars and the Pizza place…now Oscars is gone along with all the charm, at least there is still Pizza…

    • Behind that Oscar’s sign is your remembered pickle barrel Jill…

      I liked the old more humble irregular & imperfect sidewalks & telephone poles. Nothing is allowed to be weathered anymore… So much is overdesigned…

  7. This is a big part of the reason why I collect old Staples Yearbooks – great time-capsule photos (and advertisements) are a delight for those who love historic Westport info. Whenever I see this photo (I have a 1964 yearbook in my collection) I marvel at how wide Main Street appears to be – I think we must have widened our sidewalks when we went one-way.

    • You’re right — I noticed that about the road also & I remember the much narrower sidewalks


  9. A healthy balance, yes.

  10. Yes, look away everyone – nothing to see here. Your sepia tinged memories are quaint but should not be discussed. They’re disruptive. Now go enjoy our new plastic downtown and for God’s sake stop doing that comparison thing.

    • So, are you saying it is impossible to balance old and new?
      London, as an example, has done a remarkable job of it. No?

      • Don’t worry about what I’m saying.

        • I applaud what you say. I only wish others could appreciate checks and balances, and respect.

      • Hanne Jeppesen

        Europe in general seem to be able to be progressive and still hold on to old buildings. I’m from Denmark, and certainly things have changed, some stores that I use to love are no longer there, same for restaurant’s. New rides have been added to the Danes beloved Tivoli Garden, but pretty much all of the buildings are still the same as I remember, when I was growing up, and use to visit all the time, first as a child, later as a teen ager with friends. Many buildings in Copenhagen and many little towns are 300-400 years old, although they have be renovated on the inside, the outside is preserved. I came to Westport in late 1966 (Dan wrote a very nice story about me on Oct 3) as an au pair, and most likely Westport then was much like Westport in the picture, I remember Oscar’s, I remember Klein, and Ann Klein (think I bought my first American outfit there). I talked on the phone with an old friend from Westport a few years ago, one of the first thing I asked him, (he is back in the area after years away) was “How is Westport”, his answer: Westport is awful. When I asked why, his answer was, it is all chain stores. Certainly things change, and most likely we cannot stop it, some change are good, others not so much. However, I do think it is important to preserve some kind of history. It makes me sad when I go to Westport now, and see applications for tearing down historic buildings, which often is granted. Why not preserve the historic outside and just renovate the interiors?

        • x Hanne Jeppeson

          The British & American bombing of Germany *helped* w/ some of the incorporating old & new / traditional & ultra modern architecture there. (In the places that didn’t rebuild buildings *exactly* as they were — as if in Disneyland). There is a reason some of Berlin looks like *The Jetsons*. (& to forestall anyone angry at my joking about it — I am still searching for the fate of a family member that went missing “under the bombs”).

          Btw “Ann Klein” was/is a chain also.

          • Hanne Jeppesen

            My mistake, how could I forget, Anne Klein is a designer label, I meant Ann Taylor, which now is a national chain, I believe. However, back in 1967 I believe it was just a few regional stores, New Haven, Norwalk, at least that is the info I found on the internet when I searched.

    • x Morley Boyd

      Hahaha… Touché…

      Perhaps in a little while we will find ourselves in *clinics* having the latest in neurological *readjustments* (whatever surpasses lobotomy & electroshock) to prevent us from affectionately remembering former attributes of our hometown.

  11. The old times were great and thank you Fred Cantor for the photo, but it is also wonderful to think of the possibilities that are heralded by the new stuff like Bedford Square. I trust you are thinking about how great a movie theater would add to our experience. We are working on it!
    Sandy Lefkowitz

  12. Linda D. Parker

    Indeed, Dan – this is the Westport I remember! (last time I was there – summer of ’62)

  13. Hi– just started reading the posts after downloading the staples rock and roll. I think you knew my brother, Jeff Schatz (72), I graduated from Staples (66), Suzan Schatz aka schatzie. I have been trying to track down an old friend–Hatch Golden (car enthusiast) , Hillspoint Rd., younger sister — Marge. Haven’t seen him since high school, but anyone know where he is? Probably (62). Just curious. I’m a chef and Cornell PhD. Good years living in Westport . Thx.

    • Mary (Cookman) Schmerker Staples 1958

      Hatch Golden, probably a friend of my brother’s. Hatch was a nick name and his first name was Tommy. He was one of the early Downshifters. My brother was Corky Cookman. If anyone knows where Tommy is I’d love to contact him.

  14. John F. (J-period) Wandres

    Okay, Dan. Here’s your assignment. Find graduates of Stapes from the 1940s, and maybe back to the 1930s. Ask them what they remembered about Main Street. It won’t matter what they say. Each of us (me in the early 1950s) has a view of the Westport we remember. Those who came later have “their” Westport/Main Street. That is the effect and affect of Main Street on each and every one of us. Think Thornton Wilder and “Our town.” Who really cares that in the photo, that building on the Post Road at the end of Main Street has memories for me, that nobody else has. It was in Colgan’s Drug Store in 1952 that I bought my first condoms. It was in 1979, when, in a restaurant that inhabited that former Colgan’s Drug store; over white wine and mimosas, that I asked the woman who would be my second wife, if she would marry with me. That is MY westport. PeeEss: She did, by the way, and we’re still doing it. Cheers, all.

  15. No trees?! Someone will know when that changed …

    • Re. “trees”. I hadn’t even noticed that until you mentioned it.

      As someone posted earlier in the thread the sidewalks were narrower. As I recall: not so much on the East (Kleins) side of the street — but on the other side between Westport Pizzeria & Needle Park the sidewalk was very narrow w/ the telephone poles.

      People had horses & carriages when these old buildings were built — so perhaps *trees* on the commercial stretch of Main Street were the last thing that occupied their minds then.

  16. Jean Whitehead

    Thank you thank you!!!! Love seeing all the old photos. (Hmmmm, is that my parents’ car with the fins……?)