Revisiting Main Street’s Memories

The cover painting on the brochure announcing “Main Street Memories 1960” is lovely, quaint — and historically inaccurate.

It shows cars creeping north, from the Y past Klein’s and Oscar’s.  In 1960, Main Street traffic flowed both ways.

But I’m sure the rest of the Westport Historical Society show — which opens next Saturday (March 6) with a party from 1-4 p.m. — is both accurate and compelling.

Main Street, from the 1962 Staples yearbook. Klein's is now Banana Republic (and more than 1 floor); the Townly Restaurant just beyond it burned down, and the Mobil station in the distance is Vineyard Vines. Note the stoplight and 2-way traffic.

Susan Malloy — a long-time resident and philanthropist — has created a lively 4-color map.  It depicts a downtown Westport filled with locally owned shops and restaurants.  The map is spiced with quotes from people who remember that time fondly.

Susan will be at Saturday’s party.  Guests — which the WHS hopes will include newcomers as well as old fogeys timers — can chat about yesterday and today, and put their thoughts down in a special book.

In the meantime, to get the recollection juices flowing, here are a few names from the map:

Shilepsky’s Clothing
Country Gal
Rico Beauty Salon
Townley Restaurant
Tracy’s Menswear
Hartman’s Hardware
Oakes Automotive Service
Barnum Travel
Melody House Music
Dress Box
Westlake Restaurant
Swerdling’s Bakery
Welch’s Hardware
Westport Food Center
Greenberg’s Department Store
Economy Liquors
Ben Franklin Store
Pickwick Gift Shop
Isabel Eland Shop
Dorain’s Drugs
Town & Country Shoes
Charles Food Shop
Linen Closet
Bill’s Smoke Shop
Westport Hardware
Country Bazaar
Gristede Brothers Grocers

See you Saturday — right across from the Dress Box.

The much-loved Remarkable Book Shop (now Talbots). This shot is from after the 1960s -- the adjacent Record Hunter (left side of building) has already closed, and the cars look relatively modern.

66 responses to “Revisiting Main Street’s Memories

  1. Are you sure that Main Street was 2-way in 1960. I seem to recall that all of downtown streets changed (one way Myrtle in front of Bedford El, one way Taylor Place and Main Street) with the completion of the landfill in the river and parker harding parking — a few years earlier — about the time I was learning to drive.

  2. Check out the top photo. I don’t think it changed to 1-way with the construction of Parker Harding Plaza, then back to 2-way, then back to 1-way again.

  3. Charles of the Ritz. Peck and Peck. The original Bill’s Smoke Shop. The tiny original Oscar’s Delicatessen. Gristede’s & Gristede’s Liquor. Liverpool! Sigh…

  4. These were more 70s (could have also been there in the 60s but I wasn’t here then), but how about Susan Terry, the Playhouse Pub, and that little jewelry store that is now either Claire’s or Lucky… what was it? Something that ended in ______stasia? And while not on Main Street, the famous Ship’s Tavern!!

  5. The soda fountain at Ben Franklins 5 and 10, banquest of fried chicken at thee Townly Rest ., the candy wall at Bills Smoke Shop, the wood dust floor in the back of Charles Market (IGA) where the meat was cut, and the first burger machine cranked out patties. BEST OF ALL the Christmas walk where all shops were open one night , no one sold merchandise, but hot cider and doughnuts and roasted chestnuts were served for people that came into the stores to visit.

  6. Memories – I worked at Gristede’s in the md 50’s. Both my Mom and my Mother-in-law worked at Kelin’s and my bride’s first job was at Hart’s Five & Dime (don’t see that on the list). Dad always finished his work day at Wassell’s a bit ahead of Mom and made good use of the time by having a beer and visiting with Mike the bartender at the Townly. In those days, many starters at the Police Department preceded their police careers with Main Street jobs. Bob Skinner, Tony Fiore and I all worked Gristede’s under the tutelage of John Eickhoff. Ray Skinner and Tommy Lynch paid their dues with jobs at Economy Foods under Charlie Friedson. We had our shirts cleaned by Norm Lipschitz and his Mom at the Cleaners across from Klleins.
    I think Oakes Automotive was preceded by Walt Brown’s Service Station as we always stored the Gristede trucks there. Achorn’s Pharmacy located next to Gristede’s is also missing from the list. Mrs. Achorn made a great milkshake at the soda fountain there. Oscar’s made the best sandwiches ever. Chez Pierre was located down from Gristede’s and also is not on the list. Pierre Nelli was the owner and it was the best spot in town for a Chateau Brion for two. Franz Schober was the head Chef there and he now owns and operates the Waramaug Inn overlooking Lake Waramaug in New Preston.
    I purchased my brides engagement ring and wedding rings from Mac at McMillan Jewelers, another one that’s missing from the list. Muriel’s Diner was on the corner of Taylor Place but it was originally owned and operated by the Papageorge family. Colgan’s Pharmacy was on the oppositte corner next to the Ship’s Lantern. I hung out at the fountain at Colgan’s while at Staples (Old Staples) and hung out at the Ships on occasion after working a stressful shift at WPD. Beer was only 20 cents a glass in 1959-60.
    Wish I was in town so I could attend. – Dick Alley

    • THANKS for the memories, Dick. Which brings up the question: 50 years from now, will today’s young Westporters recall Main Street as fondly? Or at all?

  7. Wendy Crowther

    Hi Dan,
    As I look at the Main St. photo, I see a double yellow line in its center – a sure sign that it was indicating 2-way traffic. I think the northbound car seen in the photo has moved into the left, oncoming lane in order to avoid the pedestrian crossing the street in front of it. Look closely, you’ll see the person walking just forward and to the right of the car.

    Mystery solved??

  8. 50 years from now — will today’s young Westporters be shopping at Main Street’s
    Senior Citizen Gap? I wonder if their parents shopped at Trudy Gary? Liverpool, Gristede’s (remember Lou? He used to let me run a tab!) and Gristede’s liquor were all there in the mid-1960s. I know. I worked at Remarkable (formerly the Map & Book Store, owned by Walter Pitkin) from ’64 to ’69, and all these shops were on my daily “route.” I remember Colgan’s Pharmacy as Thompson’s. Murray and Bill at Achorn’s, who sold me cigarettes for 37 cents in 1964, while telling me to quit. Then they put up those “Smoking is Glamorous” posters and we all quit, horrified! And didn’t one of the Papageorge family (of Muriel’s) take over for Oscar at Oscar’s? David & I conducted our whole courtship at Chez Pierre, which had the best salad dressing ever created, and the freshest Little Necks for, maybe, 50 cents each.

  9. Carl A. Swanson

    Many old memories. Thanks for the listing for I would not have remembered many but for Bill’s Smoke Shop where you could get a malt and a peek at a “Playboy.” While traffic never seemed a problem back then, it does now. I wonder if they have ever thought about banning cars from the downtown area and just let people walk around. They could just shuttle people via some cutsey trolley or maybe they could just walk!

    • That suggestion has actually been floated before — several times. The protests — which arise VERY quickly — are usually of the “This is not California, what about the weather?” “People in Westport are not used to walking that far” and “Merchants would never go for it because they worry no one will ever come downtown again” variety.

  10. No one mentioned Selective Eye. I’ve seen it on other main street lists of yours, Dan, just not today. I still have stuff from there – little mementos from Bedford Jr. High days. I can’t seem to part with it. Now it seems more precious than ever.

    • I included some — but not all — of the stores that were on the 1960 map that will be at the Historical Society. Maybe Selective Eye was not yet open in 1960?

  11. Selective Eye first opened on the Post Road, directly opposite Main Street. Pebble floors, dark cork walls, I think. Sue McKenna, manager. Glorious — it was like Greenwich Village springing, fully formed, into the center of town. I’d drop my whole paycheck there without a complaint. Later it moved onto lower Main Street, but romantic memory says it was never quite the same.

  12. I think Selective eye opened in 1964 or 1965. What about the African Room upstairs above Country Gal? Later ’60s, but ’60s nevertheless. Kay Metts owned it. Really miss those days. Dan — or somebody — a book!

  13. Wendy and Dan, Oscar’s was owned by Oscar Siskin. His deli had a real pickle barrel on the floor, in the middle of the store. I was a soda jerk and short order cook at Gray’s Drug Store, next to West Lake, and across the street from Shilepsky’s, my family’s store. And who remembers the Ice Cream parlor, pre Chez Pierre?

    • Thanks, Gary, for the definitive word on Oscar’s.

      The Ice Cream parlor, of course, had three locations: The location near Chez Pierre; the anchor building in Compo Shopping Center (now Cohen’s Eye Care), and finally the building across from the old Crest (which later became Bunyan’s and is now, I think, a real estate office).

  14. Oscar Sisken. Yeah, Oscar Papageorge just doesn’t have the familiar ring. And Shilepsky’s….of couse. And Greenberg’s — I think the Gruber family. West Lake — the great and dignified Mrs. Lee passed away recently. Anybody remember Mary-the-waitress? She WAS the West Lake. And Dan — don’t get me started on hot dogs from the Crest. 2 for lunch, drowning in mustard & relish, What a loss!

  15. Linda Gramatky Smith

    How were the Shilepskys who owned the clothing store on Main Street related to the Shilepskys who owned North Main Garage (the AAA garage in town). I know the father of my Staples `60 classmate, “Skip” Shilepsky, owned and ran the garage with his uncle Jack Stein. The garage was up near Richmondville Avenue. Were the Shilepskys related? Maybe Gary Singer (above) can tell us since the clothing store was owned by HIS family.

    See you all on March 6th! So many memories.

  16. Linda Gramatky Smith

    About the Ice Cream Parlor. I know Chez Pierre preceded Tavern on Main, and I know where the Compo Acres (?) location was, but WHERE was Crest/Bunyan? One location for the Ice Cream Parlor was across from the Getty station and LCR (west of where Albe’s Furs is, and about where the urgent-care facility was for a while). Is that the third location you mentioned, Dan?

  17. Exactly. And the shopping center is “Compo”; the one across the street (Franklin Simon, Carousel, Trader Joe’s) is “Compo Acres.” Go figure.

  18. My grandmother Mabel Glynn worked at Trudy Gary’s (Country Mouse) for over twenty years. It was two doors down from Ann Taylor.

  19. Linda, here’s the Shilepsky tie-in. Two of three Shilepsky brothers moved to Westport in the 20s,Nathan and Louis. Nathan’s son Morris and son-in-law Jack Stein opened the No. Main Garage. Louis’ son Maurice and daughter Sylvia opened Shilepsky’s clothing store. Sylvia ( my mother) married Benn Singer, and had me ( in that order). Louis’ third daughter, Sally, married Sherm Jacobson who owned Gray’s Drug Store — between Walsh’s Hardware and West Lake, and
    became cosmetician to the stars of the Westport Country Playhouse. Now that’s more than you ever wanted to know about the Shilepsky’s, right?

  20. More, more, tell us more! I remember Gray’s Drug Store and Welch’s Hardware. Now somebody please fill us in on Greenberg’s, and the Gruber family?

    • My “main” (hoho) Greenberg’s memory is of the heavy snowstorm that caved in its roof — leading, ultimately, to its demise.

      I also remember the “notions” department — what a bizarre name for thread and stuff — and the creaky staircase near the back. Lots of old people worked their (in my 8-year-old mind), but they sure seemed to know their stuff.

  21. Comment from Amy Pettee Dempsey from Atlanta, GA:
    I would kill to get my hands on some of those old westport prints/posters. Can you see if the WHS carries them? or where we can get them reproduced?
    ps. this is a mission I have been on since moving to GA, and I can never seem to get down there to investigate.

    • Do any “06880” readers have an idea to help Amy? Sounds like a money-making venture for someone or some organization.

  22. I think it’s awesome that one little town can generate so many wonderful memories. If you want to pick up a book, map or walking tour guide of Westport, then a visit to the Westport Historical Society’s Remarkable Gift Shop is a must. We’ve got books with great images of old Westport as well as maps, photographs and other cool posters for purchase. Lots of fun gifts with our town Westport on it and members receive a ten percent discount on any purchase.

  23. Susan Gold’s name above reminded me of her near namesake, Susan Silver. No memory of Westport would be complete without mention of Silver’s and it’s longevity. Along with Mitchell’s, these family stores are Westport institutions. Susan and brother Steve are second generation shop keepers, know as much for their warmth and hospitality and for their expertise in luggage and a hundred other items. I love them both.

  24. The Dude Abides

    I think that art store next to where Tip Schaeffer’s and the movie theatre used to be
    is the longest standing business in Westport?
    Talk about nice people. Whew, too nice.

    • Well, “06880” readers: What do you think? Gault’s got Max’s Art Supplies beat by 100 years or so. Oscar’s and Achorn’s, right down Main Street, are older. So is Mitchells.

      Others I can think of: the Red Barn. Many gas stations. Calises. What else are we missing?

  25. Steve Simon

    Main st. two way as I recall…I know 66 H.S. post graduation morning I was driving down Main st. headed South (SE?) past Westport Hardware…so it must have been two way or I would have been pulled over, right? Sun was in my eyes as the top was down and “the morning sun is rising like a red rubber ball” was on the radio…girl and I got a good laugh at that….

  26. Linda Gramatky Smith

    Dan! You’re always so accurate, but Mitchell’s is older than Max’s? I think not. Mitchell’s was started in 1958 by Ed and Norma, but Max’s was started in 1954 by Max Kaplan. I went to school with his son.

  27. Linda Gramatky Smith

    Oops, I never said I was accurate! Max’s was started in 1956, 54 years ago.

  28. Not sure if anyone replied to Kelley but the jewelry store was Aspasia and it was right where the passage from “harder parking” comes out. I did not read all these posts intimately so sorry if redundant but from a Staples ’79 perpective I remember:
    The two places to clothes shop when I was little were Trudy Gary and Zabins.
    Later: Country Gal, Gold Rush (love those boot cut cords), and sometimes Selective Eye (I remember getting a pair of jeans there for $2.90 once on sale), also Exit 18, Dress barn and the Fairfield Store.

    Fond memories of Sally’s record dept in Klein’s (and thank God we can still see her in her own store) Carousel, of course Esther and Sidney Kramer at the Remarkable, The Big Top, The Ice Cream Parlor, The Farm Shoppe.

    Working at the Playhouse we always went out to Ship’s. If we wanted food the kitchen was closed (except if you were Shaun Cassidy), if we wanted just drinks we had to order food.

    Silvers must be pretty old, isn’t it?

    What about Chubby Lane’s?

    When we were little the Merrit Superette was a big deal, though we called it “the corner store.”

    Love those Westport memories!

  29. Gary Singer

    Have we forgotten Brown’s Gas station? Smack in the center of Town. And you could get to it in either direction then.

  30. We blew through Westport a few days ago, did our religious pilgrimage up Main Street — and thought we noticed that the Liquor Locker was gone. This can’t be true — someone tell me we were wrong.

  31. The Dude Abides

    Yeah, I forgot about that Brown gas station. There was a Texaco station where Ace Hardware is as well.
    But I been around since 1953 and I remember Main Street as two lane,both directions. Before the land fill parking area, you had to access the library and YMCA via Main Street if you were coming down from Cross Highway/North Avenue. As to its original site, I still think the art store has been the longest lasting. Gault doesn’t count cuz it ain’t downtown and I don’t think Oscars was orignally where it is now. Not sure about Achorn Pharmacy?

  32. Oscar’s and Bill’s were side-by-side in small, narrow storefronts (where the pizza place is now), alongside a little alley. Oscar’s kept its flavor after moving to its larger space; my memory is that Bill’s lost something when it moved across the street to bigger quarters. Speaking of that space — when was Brooks Corners built, and what was in that space before? And when was the Klaff’s building constructed? IWestport Pharmacy & the World Affairs Center were there in 1961, across from the old Library, adjascent to Taylor Place.

  33. I think Achorn’s remained in the same spot –next to Gristede’s. Might have just got bigger.

  34. I was working late at my desk in the WAC and saw the wires flash that started the fire, in a little alley behind Muriel’s. Stayed and observed the whole event. There might have been an older Klaff’s building that then was rebuilt afterwards — not sure. We always called it “the Klaff’s fire.”

  35. The Dude Abides

    I now remember a pharmacy where Tiffany’s is now and the bar was there later as well. I think that was Achorn Pharmacy. Could get a cheery coke and fries (with tons of ketchup) after you WALKED downtown from BJHS. This would be 61-63. I am holding firm that the Art Store has been downtown in its original spot for the longest. That is what the owner told my anyway. But whatever, the dude abides. Don’t want to get that huffy gal from Minnesota mad at me again!

  36. Right. Thompson’s. No question. Achorn’s has always been exactly where it is now. There was a redheaded woman who worked behind the lunch counter at Thompson’s. After Thompson’s closed, she turned up behind the lunch counter at the Weston Pharmacy. Until they closed the lunch counter, which to us was The Beginning Of The End. I agree on Max’s. It was there in ’61,

  37. Kim Crowther Manning

    Thanks to Leora who answered the question about Aspasia. That’s been bugging me for days! (I was class of ’80, btw, so I remember much of the same things you do…). Maybe you can remember the name of the Indian clothing store that was either to the right or the left of Klein’s (Wendy Crowther – you should remember this!) where we got our famous “Hirachi” (sp?) sandals back in the 70s. I worked at the Selective Eye for awhile. I can still smell it! Last I knew the sign for Selective Eye was hanging outside of United Houswrecking in Stamford – not even sure United Housewrecking is still in business, but wouldn’t it be great if someone could get their hands on that sign for Saturday’s event? Remember Functional Clothing where you could buy used jeans? The Plumed Serpent was next to Bill’s Smoke Shop (it’s now in Playhouse Square and primarily a bridal shop) where so many girls bought their Gunne Sax prom dresses! There was also a little variety store just next to the alley way by Ship’s where we’d buy fireballs and candy necklaces before heading to catch the minny bus at Jesup Green – can’t remember the name of that either but I seem to remember being scared of the old man who ran it. Wish I could go back in time for a day to experience all of that again… oh, and in answer to Wendy’s question if it hasn’t been answered already, the Liquor Locker is still there!!

  38. SO relieved about the Liquor Locker. It’s not the product — it’s the idea that it’s virtually the last of its kind. Oh — the Indian store was Rachna of India, I think. I can picture the owner’s face and it’s swimming in fabric with tiny mirror! All the dresses smelled of incense — or am I making that up? I think the variety store you’re talking about the Westport Smoke Shop, and the guy you were afraid of might have been named Carmen. Edna, who owned Functional Clothing, was the coolest storekeeper in Westport.

    • Carmen is right — I was trying to think of that. And Edna Boden (?) ran a great shop. She sold used jeans for low prices. Today you can buy new jeans that LOOK new for high prices. Go figure.

  39. Kim Crowther Manning

    Rachna of India! YES! And yes, now I remember it was the Westport Smoke Shop – we just called it the Smoke Shop. I thought I might be getting the name confused with Bill’s Smoke Shop. Edna’s last name was Boden, although I think it might have been spelled Bowden. She had a handsome son named Scott (?).

  40. Gary Singer

    My cousin, a native Westporter, just reminded my that the restaurant between Gray’s Drug Store and the old Library, was the “Old Canterberry” before it was West Lake. I had forgotten that.

  41. Gordon Dalton

    Hey Gary Singer. Remember me? a nd thd the westport playhouse? I’m trying to make a contact and perhaps you can help me. I’m trying to contact Sue Bernhard Bissell without much success. I’ve got a Photo Album that I think she might like to see. Need her address or email. Can you help?

  42. My brother was a singing waiter one summer at the Players’ Tavern. Also, I saw Dizzy Gillespie there once about 35 years ago. He walked up to my table and leaned over and told me I was beautiful and that he loved me! Enjoyed telling my husband that when he arrived…late.

  43. To Gordon Dalton: Of course I remember you, pal.
    And yes, I have Sue’s address and phone number. Coincidentally she’ll be at my home in Saratoga next weekend (4/2-4). Please call Dan Woog for
    my e-mail address.

  44. Gordon Dalton

    Cheez guys, this blog made me a success! I made contact with Gary thanks to falling by chance into the blog and being rescued by Dan Woog and Gary. See, it pays to be pushy! Incidently I lived in Westport or environs from 1962 until the early 70s and Main St. was still two way when I left. Westport is a town that never leaves your being. It’s as if its dust-motes blend with one’s cells and they are tainted forever. anyway thanks for your blog when I needed it!

  45. How can I get one of the 4-page maps. Thanks.

  46. If you mean the brochure that Susan Malloy conceived and drew, I saw them at the Westport Historical Society gift shop for 75 cents. You could call them to make sure they still have them.

  47. This photo might be of a help. Taken on Main Street – Memorial Day 1962

  48. Pingback: By Committee | Craig Fehrman

  49. Oscar Sisken was my grandfather. I remember bringing sandwiches up to the cash register for the customers in what was Oscar’s Deli, the cash register being operated by my Grandmother, Sally. Those were the days!