Oscar’s Ends Its Run

Oscar’s Delicatessen — the last “mom-and-pop shop” on Main Street — will close on Monday.

The only casual dining spot on the street — which dates back more than 50 years, when it opened a few doors away from its current location — has been owned since 1971 by Lee Papageorge. He’s currently battling lung cancer.

The announcement on Facebook included this photo of the barber chair in which owner Lee Papageorge traditionally sits.

The announcement on Facebook included this photo of the barber chair in which owner Lee Papageorge traditionally sits.

A brief announcement on Oscar’s Facebook page says:

After 42 years Oscar’s will be shutting their doors permanently on Monday, August 1.

On Sunday morning customers will be sharing memories and stories with each other.

Thank you for always supporting local family run businesses.

Thank you Lee Papageorge for giving people second chances and for always loving your extended family.

Thank you.

It’s an abrupt end to a Westport icon. “06880” joins Lee’s countless fans and friends in sending thoughts and best wishes to him, and his family.

Oscar's owner Lee Papageorge.

Oscar’s owner Lee Papageorge.


55 responses to “Oscar’s Ends Its Run

  1. Bobbie Herman


  2. This is such sad news. Thank you, Lee, for all the happy memories and great food, service and friendship at Oscar’s. One of a kind! God bless you, Lee.

  3. Charlie Taylor

    Countless great meals and great company at Oscars. The very Soul of Westport.
    Love and thanks George
    Charlie Taylor

  4. Janette Kinnally

    I am so sad to hear this! Lee and his family were wonderful to deal with every time I went there. I cannot believe they are closing on Monday.
    So glad you shared this with us. I want to make sure to go to tell the what they meant to Westporters over the years. We will miss them immensely.
    Thanks again Dan for keeping 0688″ readers informed!!!

  5. Ana Johnson

    In the 80’s my father, sister, and I used to come to Oscar’s for lunch every Saturday. We were there so frequently that when they painted the mural on the long wall, we thought my father was one of the people in it (and even when we realized it wasn’t him we still liked to pretend it was). It’s been a long time since I’ve eaten at Oscar’s but I am so appreciative of the deli for what they’ve contributed to the town and for our own family memories. This is the last place on Main Street that I remember from growing up and it’s sad to see that chapter close. I know it’s unlikely but would love to see another more updated sandwich shop/deli in the same space. Keeping a little bit of the old style Westport in new Westport. Best of luck with your battle, Lee.

  6. Mary Hoffman

    Who owns that space? Every Saturday my kids would go to Oscar’s with their Dad. My daughter still looks forward to coming home, going to the gym with her dad, and then off to Oscar’s for a turkey sandwich. Thank you Oscar’s for 25 years of happy memories and delicious turkey sandwiches. All of you will be missed, the guys behind the counter and the women who take care of the tables. And of course Lee, he always had a smile on his face.

  7. Suzi Desmond

    Sending hugs to Lee Papa George who is the heart and salt of Westport 💐
    What a great family greeted us for so many years!☀️ We will all miss the meeting spot .. the food was always delicious and the art was fabulous !!
    Great memories were made at Oscars !!

  8. Betsy (and Dan) Kahn

    My First Lunch DATE in Westport was at your place… Picnic at the RIVER
    Best Cole slaw, maybe Ever! We beg you to stay 😀

  9. So many friends were made at Oscars, from behind the counter, to the special needs workers with the biggest hearts, to the regulars… And at the helm was Lee…. This is a very personal loss for not only myself and family but for the town… Main ST … And the heart of Westport…. Mary, Allie, Missy, and of course Lee… Thank you for your friendship generosity and being stewards of how downtown was…. Lee fight the good fight…. You are very missed

  10. Marcy Sansolo

    Well I know where we’ll be having lunch today and tmrw. The folks at Oscars are the best, and will be missed. Godspeed Lee & thank you.

  11. This makes me so sad. Lee and his family were a bright spot of locals on a Main Street that has turned into a mall of corporation-owned shops (with a few notable exceptions, particularly The Brownstone). I will always remember our first Westport lunch, from Oscar’s as the moving van was unloaded at our very first home, back in 1995. Thank you, Lee, for being such a happy and loving part of our town. Wishing you the very best and a full and speedy recovery as you battle your illness.

  12. William Adler

    Thank you to Lee and the entire staff. Oscar’s has a special place in my mind’s eye of growing up in Westport along with other icons like Mario’s and Manero’s. Oscar’s *is* Westport. Thanks for posting, Dan.

  13. Susan Huppi

    Best wishes to Lee and his family. My family has fond memories of Oscar’s. It was always like going back to childhood to eat there. A true Westport landmark not only physically but emotionally!

  14. Samuel Goodman

    It is with profound shock that I learn about the closing of Oscar’s and Lee’s illness. When I was down on my luck, Lee gave me the chance to thrive. I will never forget his support. Now it is my turn to send him and his family my best wishes for a full recovery. The Town of Westport will never be the same. Thank you Lee for being such a great guy.

  15. Juliana Sloane Fulbright

    Well, Oscar’s is closing , may as well leave Westport now. No reason to go to Main St anymore. Best wishes to Lee and his family,it’s a tougher time for them than for us. I have been going to oscar’s since it was a few doors down. I met friends there for lunch and our family went there a lot when the kids were little. It will be sorely missed and so will the Papageorge family.

  16. Mary Palmieri Gai

    Oh no. Saddest closing news ever. Many firsts there for me. First time I had a bagel or tasted cream cheese. First time ever having potato salad and first time having a sandwich that tasted so good I thought I was dreaming. They are like family and fed each of my family members so well over the years. They treated us all so well. I’m so sad…I wish this was an April fool story.

  17. Lee and the folks at Oscar’s are a unique and special part of hometown Westport. Lee gave my three year old a tour of the kitchen and showed him where he kept the pickles and hid the money. I bring my cousins there when they visit and my mom for lunch when she is here from Oklahoma. Lee hosted my first art show and helped launch my photography business in Westport. My boys are old enough now to enjoy eating up at that little table in the window by themselves. Thank you to everyone at Oscar’s, your smiles and your When Sally Met Oscar special will be sorely missed.

  18. Dawn Wallant

    Noooo! Say it isn’t so!!! Loved this place!

  19. Bruce Schneider

    Very sad that Lee is so sick and the decision to close. For the sake of Westport and Oscar’s employees and customers, I was hoping that someone else, like Gold’s, would take over the management until a permanent manager could be found.

  20. Laurence S. Untermeyer

    A sad, sad day for Lee his extended family and all of Westport…Larry Untermeyer

  21. Mike Stuttman

    Lee, thank you for all the years of great food and company. Oscar’s will be sorely missed. Please get well soon and enjoy your well deserved retirement.

    The Stuttman Family

  22. Kempton Coady

    I am so sorry for Lee. Rosita and I have been going to Oscar’s for 40 years. It is a mainstay of Main Street. Kemp Coady

  23. Wendy Crowther

    This is sad on so many levels. My heart goes out to Lee and his family (including his family of employees). Generations of Westporters will continue to memorialize Oscar’s as they tell stories in which this great eatery and meeting place served as a core setting. Thank you, Lee, for all you’ve done to help Westporters, both old and new, learn what good food, good service, a friendly smile, and a neighborly vibe can do to create and proliferate a comforting, reliable sense of home.

  24. So sad. That was the heart of Main Street! Will really miss The food, Lee, the great people who worked there, and knowing it was there. We pray for Lee’s health!

  25. Don Bergmann

    A lovely place, a lovely man. At this point, Lee’s well being is foremost.
    Don Bergmann

  26. I grew up in Westport and was an Oscar’s regular with my father from early childhood. After.
    college and law school I lived in different parts of the country – Minnesota, North Carolina, California. Each time I came home to Westport there was one not-to-be-missed constant: Oscar’s. I loved the smell of Oscar’s, the friendliness of its staff, the pickles, the matzah ball soup and the thick sandwiches. I am so sad today to know that Oscar’s will be no more.

  27. Oscar’s became a family to us when my husband and I moved to Westport 25 years ago. I knew no one in town, but I knew that Oscar’s was where locals went. I met a small group of regulars and we became fast friends, meeting for coffee every week. They threw me a bridal shower, they visited me when I was pregnant on bedrest, and Lee and MaryJo’s girls Ali and Missy babysat for us. The Papageorge family is beyond warm and loving, and to this day they, along with their amazing Oscar’s extended family, still welcome us and our (now grown) kids. Though our trips are less frequent, Oscar’s will always be in the tapestry of our family’s life. Lee IS Oscar’s and most important we wish for his return to good health. Sending so much love to all of the Papageorges and to the Oscar’s terrific employees. Thank you for so many years of being a part of our family. Oscar’s will be sorely missed.

  28. My heart goes out to Lee and his family. Is there any other reason to go to Main Street? Unless the landlord is an obstacle, why is it not for sale? I know people who would jump at the opportunity. Ten years from now are we going to form a commission to bring a deli back to Main Street? “The Westport Deli Initiative”

  29. Sandra Johnson

    Another sad happening in WP However, best to you Lee and your family — you served the town well!!! All of us have many happy memories. You will be missed by all the many you touched! Main St will definitely be changed.
    It has slowly been changing for years which is also sad, BUT as the saying goes “Time marches on” and , many changes march with it!!

  30. Robert Mitchell

    To Lee, a true supporter of the Town of Westport, on behalf of Westport Historical Society, and my family, all best wishes during this difficult time.

  31. So sad in so many ways. Always a go to spot to take visitors to town, full of “Westport” memories! Always a stable part in our very changed town! A tremendous loss to Westport and it’s community spirit!

  32. Such sad news on such a great run! My thoughts and prayers go out to you Lee and your family. May you overcome this setback and successfully recover from your condition in good health and with much joy and happiness that you gave to some many of us.

  33. Julie Van Norden

    This is one of the saddest moments in my personal history in Westport. I’ve only been here 14 years so I didn’t know Westport when it was a real town versus an open air mall. Oscar’s was the place that kept it real for me. I wish Lee and his family all the best. Good-bye Oscar’s. You will be missed😢😢

  34. Barbara Ryan

    So saddened by the news. Sorry to hear about Lee and our wishes and prayers go out to him and family. Hate to see Oscar’s leave. Had some really great meals. Downtown won’t be the same.

  35. OH KNOW! It’s been well over 60 years–I’d go with my dad to Oscar’s, a shop no bigger than most folks’ closets today, to pick up Sunday supper since it was the only act in town opened on Sunday back in the 50’s. Best of good wishes to your complete recovery! Oscar’s will be sorely missed. What I’d do to be there this weekend to relish a corned beef sandwich and a dill pickle–but I’m here in Naples, FL.

  36. Wow, talk about end of an era! How sad…:-(
    Wish I could order just one more roast beef on rye! I remember when Oscars was in the little tiny spot near the Wspt Pizzaria…My Dad would take me there and let me get a pickle out of the big barrel to go with my Roast Beef on Rye sandwich. Nobody else ever came close to an Oscars Roast Beef sandwich anywhere else!
    Best of luck to Lee with his health…it seems like the folks who give the most of themselves should have only the best of luck and health in their lives.
    I hope somebody steps up to the plate and opens a comparable deli on Main St. They would have big shoes to fill for sure!
    Thank you Lee and family for lots of great memories!

  37. Deb Rosenfeld

    Wishing you, Lee, a full recovery. Our first lunch in Westport, 40 years ago, was at Oscar’s on the recommendation of our real estate broker. We will miss you, the staff and a great roast beef sandwich on Main Street.

  38. Linda (Pomerantz) Novis

    Thank you Oscar’s for being on Main Street so many years!
    My family in Weston went to the original ‘Oscar’s’ a couple doors down Main Street..(it was no bigger than a closet,then..Oscar was a nice man,then.. as the ‘Oscar’s’
    staff through the years,afterwards,all good folks.
    I used to stop in there for bagels,en route from Mass. to visit my mom in Stamford. (Oscar’s bagels Always better than anyplace up in Massachusetts…)

    Best wishes to Lee.


    Prayers and healing light for Lee Pappageorge and his family.

  40. Jean Whitehead

    All best wishes to Lee and his family and staff.
    Thank you for everything you gave to our town
    over the years.
    The Main Street we remember will live on in our memories.

  41. Anthony Palmer

    Sad to hear the news of the closing and Lee’s health problems .

  42. Kelly Copeland

    All the best to the Papageorge Family and everyone at Oscar’s. You made Westport a special place!!!

  43. Ali Papageorge

    We are overwhelmed by all the love and support for oscars and my dad!! Xoxo

  44. We came to town today just to say goodbye. Couldn’t get in the door but our thoughts were with all of you. My son, Josh, loves his trips to Westport and Oscar’s is the only non-burger shop he will eat at! Lee and all of the staff are never anything but nice to him and my entire family!

  45. It is hard to express the sadness that I am feeling for Lee and his family.Many prayers to you, Jackie Frost, Staples class of 70

  46. Brad Muscott

    This is truly the end of an era in Westport. Such a wonderful legacy, yet so sad. And never to be forgotten.

  47. Tom Feeley Sr

    Lee…thanks for the memories !! You’re the best 🙂

  48. I just started coming to Oscar’s when I started coming to Westport a lot last year and it’s been my go-to place for roast beef sandwich, potato salad and Cel_Ray every time I’m here. Great food, great service. Healing thoughts and know that this newcomer will miss this place terribly.

  49. Peter W Nathan

    The “ROMEO’S” will miss their weekly round table lunch group get together. Thanks for the pleasant memories, excellent service and good food. And best of luck, Lee. Get well and make it happen.

  50. This is so sad for many reasons! First for you Lee and your family. My family and I loved going to Oscars for lunch, treats and loved in the recent years going to “The Oscar’s”. All the people that work there are so wonderful and you made it such welcoming place to be, whether alone or with family and friends. My prayers are going out to you and your family. Wishing you peace, health and healing.

  51. Westport will never be the same! Westport was Oscars!
    Lee and Mary thank you for my forty years of memories. Why do I have a vision of it re-opening with Lee back in the red chair holding court once again?
    Liz Fuller

  52. Debby Grant Josephs

    My Staples class just celebrated our 50th reunion and Oscar’s was a part of all of our lives in Westport. I now live in Asheville, NC and couldn’t be there for the reunion. However, my son and two grandchildren, traveling back to Asheville from a camping trip going as far as north as Montreal, stopped in Westport a few weeks ago to bring back with them some Oscar’s goodies to us here. Knowing now that Oscar’s will be no longer be there I am especially grateful to have had a cooler full of pastrami, corned beef, bagels and lox as a final celebration to an amazing and wonderful Westport landmark.

  53. Thought you might be interested in a little history of Oscars along with a photo of their original location:

    Oscars 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 used to come in early in the morning and make the potato salad and cole slaw for the week. I believe he also made his own pickles which were sold for a nickel each! In those days the rolls and bagels were 5 cents each and a loaf of rye bread was 29 cents.

    In later years Benny was unable to work so Sally’s nephews, Peter and Harold Epstein used to help out Oscar. (Interestingly, their father was Sid Epstein who used to manage Maxine Furs which was diagonally across the street in the far right-hand storefront in the Brooks Corner building.) When Oscar was ready to retire he sold the business to Joe (I forget his last name), 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, at some point, hired Lee to help him. When a rumor started circulating the Gold’s Deli was considering opening on Main Street, Joe decided that it was time to expand before Gold’s came in and took over. That’s when he moved Oscars to its present location. When Joe retired and moved to Florida, he sold the business to Lee.


  54. Inglis Hale Sellick

    So sorry to hear of Lee Papageorge closing Oscar’s but especially wanting to wish him well during his battle with illness. We have had so many happy times at Oscar’s , as recently as 2 weeks ago , returning to Westport to visit friends and looking forward to our favorite roast beef sandwiches, spontaneous political discussions on the terrace . Putting all the children in the car during a snowstorm / power outage and heading downtown to Oscar’s and seeing familiar faces….lovely staff and friends . We will miss you, alas Westport is changing, I am so glad I knew it when….Inglis Hale Sellick