Friday Flashback #218

Opening a new restaurant in Westport is never easy.

Opening in the midst of a pandemic is especially tough.

But Hudson Malone did it. The steakhouse-and-more is drawing raves with its menu, Westport-themed decor, and comfortable, COVID-conscious ambience.

Hudson Malone took over the former 323 restaurant — named for its Main Street address, across Canal Street from Coffee An’.

That’s been the site of many restaurants. Before 323, it was Bogey’s. And before that, Oliver’s. And before that …

… well, that’s this Friday’s flashback. If you can name all of Hudson Malone’s predecessors — or even any of the others — click “Comments” below.

BONUS QUESTIONS: How about all of the restaurants that once occupied Shake Shack? Or the Sotheby’s real estate office at the Post Road East/Myrtle Road intersection, which for many years housed many eateries? Dig in!

(Hat tip: Steve Crowley)

44 responses to “Friday Flashback #218

  1. joyce hergenhan

    Shake Shack was Tallulahs

  2. Stepping Stones or Stones Throw.

  3. I’ll take the bonus….

    Before Sotheby’s I remember Glynn’s Cafe.

    Before Shake Shack I remember Deja Vu (a lot of police calls), a Chinese restaurant (can’t remember the name) and way back Beefsteak Charlie’s.

  4. Shake Shack was also a marvelous Thai place. Pho Mekong? I miss it.

  5. Shannon McCarthy

    William Pitt – GLYNN’s Cafe
    Shake Shake – Beef Steak Charley’s????

  6. Sotheby’s was Glynn’s Cafe, a great place for Fellowship Hour after Thursday choir practice at C&HT.

  7. William Scalzi

    Before Glynn’s Cafe, it was Cherry Street West

  8. Kathryn Sirico

    Sotheby’s way back La Crepe

  9. It was an antique shop for awhile. One of my photography friends lived upstairs then. The other place I remember as Glynn’s with Spike the bar tender and La Crepe where my French teacher from Weston worked

  10. Pitt was also “Matthew’s” in the early eighties.

  11. Shake Shack will always be Beefsteak Charlie’s to me.

    • John D. McCarthy

      Unlimited watered-down beer, wine and sangria was a big draw for high schoolers, if I recall correctly

  12. Way before Bogey’s….Cross Roads

  13. John D. McCarthy

    Shake Shack was Beefsteak Charlies in the early 80s

  14. Going much further back than anyone so far, I remember this as Daley’s Store (maybe Daly). My friend Charles lived nearby on Canal St. and we would buy candy from Mr. Daley and then go play in the gravel bank that later became Woods Grove. About 1940.

    • So Peter: was the commercial strip across the street (where the Merritt Superette was) built by 1940? And, if not, do you remember roughly when that came into being? Thanks.

      • Carl Addison Swanson

        The “Merritt” was there in 1952 when I discovered the candy section along with a dry cleaner, liquor store and Texaco gas station where ACE was at and Westport Hardware after that. Despite walking home from the YMCA nearly everyday, I have no recollection of what was located where Bogey’s was despite seeing the name(s).

  15. Larry Holtgrewe

    Crossroads was THE place to hook up and had awesome “dinosaur ribs” on ribs nite. I must have dropped $10K there……😎

  16. “The Corner Bar” was the first name I recall prior to Cross Roads. I must’ve looked old from my age, as I was served a beer at age 16 there. (This was prior to the legal drinking age dropping from 21 to 18, back in 1971). So Hudson Malone, 323, Bogey’s, Oliver’s, Cross Roads, and then before that The Corner Bar. I liked them all. Good luck to H.M. I hear it’s great.

  17. Gloria Gouveia

    It was also Maud Chez Elle. It was one of three locations: Westport, the West 50’s in Manhattan, and Paris, France.

  18. Clark Thiemann

    Wasn’t Shake Shack a nightclub that kept getting shut down for various reasons?

  19. I spent many Friday and Saturday nights there when it was ‘Crossroads’ featuring disco music and yes, guys wore bell bottom slacks and wide collar disco shirts. One night in the mid -1970’s a group of us wanted entry but one friend was wearing blue jeans which were against the dress code. The bouncer insisted he couldn’t enter. It happened my friend had been class president at Norwalk HS in 1968 and fought the school administration to allow blue jeans (remember…this was Norwalk H.S! ) successfully. I began to argue with the bouncer. “So,,if he’s wearing any long pants other then blue jeans he can come in?” I asked. The bouncer answered in the affirmative and I had an idea. We went to my van and pulled out a set of yellow bib foul weather pants I wore when sailing in bad weather. He put the bibs on and went to the door. “You said anything except blue jeans”, I reminded the bouncer. He smiled… “Go on in”.

  20. Jimmy Stablein

    Going in reverse:
    Hudson Malone
    Bogey’s Grille & Tap Room
    Stone’s Throw
    The Corner Bar
    Maude Chez Elle
    A fish market (name unknown, please advise)
    What was before these ? HELP !!

  21. What I recall is that one of the restaurants at 323 Main St was co-owned and/or operated by a Staples classmate, Dan O’Grady, who was a soccer teammate at Coleytown Jr High and, if my recollection is accurate, was a track star at Staples.

    In any case, the restaurant’s decor included framed reprints of some famous Neil Leifer photos and other Sports Illustrated pictures. For whatever reason, I remember a great one of Juan Marichal doing his high kick and another iconic one of Ali standing over Sonny Liston. I can’t begin to tell you what years that version of the restaurant was there—but I remember the sports photos.🤨

  22. Bogey’s was our go-to restaurant. We named our last dog Charlie Bogey, He lived longer than both Bogey’s did.

  23. Bogey’s had the most incredible burgers. After a flood from a hurricane (Irene?) caused them to close, they opened in Norwalk, but unfortunately, that didn’t last too long.

    And do you remember when Tiffany was Ships?

  24. Mary Ann Batsell

    One of the names of the restaurant was Crossroads, it was owned by
    Andy Wilhauer and it was one of the most popular restaurants in Westport.
    As for Wm Pitt Sotheby’s most notorious restaurant was Le Crepe owned by Barry Trupin.

  25. Jimmy: In the 1950’s 323 was a tea room run by the Chucka family who also had a small catering business (later relocated to Riverside Avenue). When my brother and I were little our mother regularly took us there for an egg salad sandwich and a Coke.There were old wooden plank floors and a juke box. Most vividly sitting in a corner was a regular…always reading a book. Marilyn Monroe.

  26. correct Dan. My spelling at 213 am is not always reliable. 🙂
    I went through school with their son. Very nice family.

  27. kathleen Dehler

    I remember every Friday night during Lent We would “suffer” and go to Olivers (no meat on Friday) and order the Crab Legs..Huge portion for $7.95! That was penance!!!!!???? We loved Lent!!!

  28. Richafrd Marcus

    I cooked there when it was Maud Chez Elle back in the late 60’s, early 70’s.

  29. Corinne Wohlforth

    Doolitte’s prior to Olivers; Le Crepe was restaurant prior to
    Real Estate office corner of Myrtle and Post Rd

  30. Jennie G Pickering

    I’m here for the bonus question, probably a day late a dollar short!:
    1. restaurants that once occupied Shake Shack? Beefsteak Charlie, and some random Thai restaurant

    2. the Sotheby’s real estate office at the Post Road East/Myrtle Road intersection? Glynn’s for the win!

  31. Sotheby’s was Joshua Tree back in the mid to late 1990s

  32. Before Maude Chez Elle and Tidewater Fresh Fish it was a Westport RedCross office locale in the 50’s.
    .Soon after that, Jack Stein and Morris Shilepsky operated North Main Garage..a (kosher) Mobil station- where I pumped gas…for almost a week.

    But my best memories, other than playing there w Charlie Karp (@ 323)
    was hearing two good “unknown”singers at Crossroads in the early 70’s:
    :Natalie Cole, and Bridgeporter Laurie Beechman.Her rendition of Midnight Train to Georgia”was enough for me to think- “that voice is goin’somewhere”
    It did …Cats lead on Broadway…. and her own 42nd Theater.