The Original Oscar’s

As Westport grapples with the closing of Oscar’s — the last mom-and-pop place on Main Street — alert “06880” reader Jim Gray sent along a photo of the original deli, a few doors down.

Oscars - original

Oscar’s next-door neighbor — Westport Hardware — burned to the ground in 1976. It’s now the site of the 3-story Gap building.

Jim recalls:

Oscar’s started out with a real Oscar. Oscar Sisken and his wife, Sally, ran it for many years along with Sally’s brother, Benny. They drove in from Bridgeport, and were open every day from 8 am to 6 pm with the exception of Wednesday.

On Wednesday Oscar came in early, and made potato salad and cole slaw for the week. I believe he also made his own pickles, which he sold for a nickel each! In those days the rolls and bagels were 5 cents each. A loaf of rye bread was 29 cents.

In later years Benny was unable to work so Sally’s nephews, Peter and Harold Epstein, helped Oscar. (Their father, Sid Epstein, managed Maxine Furs diagonally across the stree.) When Oscar was ready to retire he sold the business to Joe Milici, a hair dresser who worked at a salon a few doors down the street.

Joe ran the business from the original location for several years, and hired Lee to help him. When a rumor circulated that Gold’s Deli was considering opening on Main Street, Joe decided to expand before Gold’s came in and took over. That’s when he moved Oscar’s to its present location. When Joe retired and moved to Florida, he sold the business to Lee.

16 responses to “The Original Oscar’s

  1. Alice Crowther

    Thirty years worth of friendships have resulted from occupying the tables at Oscars. It started in classes at the old Y and carried over to coffee and bagels afterwards at Oscars. We solved family issues, diagnosed health conditions, planned children’s weddings, held therapy sessions and were supports for each other during the hard times. Oscars was our place to laugh, cry, complain, console, and just be together in a “girlfriend” kind of way. Silly as it sounds we laughingly referred to ourselves as The Oscarettes, I attended the gathering at noon today to say my last goodbye and heard Imus, our favorite waitress say, “Sure I can get another job but I’ll never be fortunate enough to have another boss like Lee.” That says it all.

  2. Fred Cantor

    Wow, I’d never seen a pic before of this section of Main Street during this era. What year if this (if you know)? Thanks.

    PS–so the Westport Hardware space became Sloan’s Furniture at some point?

  3. Yes, Westport Hardware became Sloane Furniture.

    • Dorrie Barlow Thomas

      ah, yes, Sloane Furniture (thank you! THAT was the name! I could NOT come up with that) I remember that fire…my father & I watched it from Parker Harding…as an 8 year old, it was a fascinating thing to see; I remember watching them throwing mattresses out the top floor windows.

  4. This picture was taken in 1954.

  5. Great story! Keep history real and current!

  6. Sharon Paulsen

    Love seeing old pics of downtown!

    I don’t remember the Westport Hardware fire in ’76. But I was 7/8 then.

    All these posts about Oscar’s last few days are really great Dan! So sad to hear it’s over – the last bastion of Westport mom ‘n pops. (Except for maybe the Pizzeria – and, is Achorn’s still around?).


  7. Sharon Paulsen

    Ah yes, got it Dan, thanks for the reminders/article links!

    Dorrie, you actually got to see that fire? Soooo cool, lol! I’m racking my then 8 year old brain to remember any of the wreckage or rebuild. Oh well.

  8. Bonnie Bradley

    And, does anyone else remember when Achorn’s was on the Post Road across the street from the old library? When Klein’s, Shilepsky’s Dry Goods, Welch’s Hardware, Gristede’s market, Greenberg’s, Dorain Drugs and other mom-and-pop stores were all fixtures on Main Street? And Colgan’s Drugstore, with its popular soda fountain with coveted stools, was a fixture on the corner that now houses Tiffany? And when, before the river was filled to build Parker-Harding parking, those stores on the west side of Main Street each featured a pipe extending out over the river, active when a toilet was flushed inside. And when women and girls were restricted to entering the YMCA through a discreet side door on Main Street, never through the front door. Ah! The good old days.

  9. Joyce Losen

    So so sorry to hear of Oscar’s closing. Haven’t been able to get downtown lately due to my own accident, otherwise I definitely would have been there to say goodbye. Used to eat lunch there several times a week before I retired. My best to Lee and MaryJo. I remember their girls working there when they were in High School. I, too remember the original Oscars and Sloane’s (it was an outlet). Then a bank came in that had a tall clock outside.. Was there more than one fire? The fire I think I remember was in the 60’s It was the one that burned down the bank and the offices above it. I worked for the Westport News then and it was probably the most dramatic news story I “covered.”.

    • Was that the County Federal bank? I don’t remember a fire there.

      • Susan Hopkins

        Yes, Dan. County Federal Bank. I banked there back in the day. If I’m not mistaken, “Soup’s On” was nearby. Another enjoyable eatery. Thank you for your coverage of Oscar’s: It’s rich history through the years … to its sad conclusion. Au revoir, old Westport.

  10. Arline P.Gertzoff

    Oscar’s was a regular Sunday stop in days of yore. Sally actually made the best potato salad I have ever eaten. My best Oscar story goes as follows.The lady in front of my father says to Oscar she wanted center cut pastrami, center cut corned beef, and could she please have the heart of the Swiss cheese. If only we had selfie’s back then. Oscar’s glasses slide off and I still remember the look on his face. When she exited everyone burst out laughing and sorry I can’t print Oscar’s reply.
    My prayers are with Lee. Not all may know that Lee’s grandfather ran the old green diner opposite the old Westport Library on the corner with Taylor Place. Now all the deli mavens can go to Gold’s, head for NYC, or hope Zabar’s opens a Westport outlet. In the old days my grandfather would get salami and other deli treats, wrap it in newspaper, and bring it every Friday night when he came to do the tailoring for Comet Cleaner’s my late father’s business on the Wilton Road. Those were the days. Great memories.

  11. Amy L Kaplan

    When we came to Westport in 1956, Oscar’s with it’s original owner, Oscar, was located in Compo Shopping Center where Gold’s is today. My father (Max’s of Max’s Art Supplies) and I went every Sunday morning to get bagels and cream cheese and lox. Oscar would give me a black and white cookie to eat while waiting in line so that I wouldn’t get impatient. Another part of Westport is gone.