Friday Flashback #58

Last week’s Friday Flashback featured an intriguing aerial photo of downtown Westport, circa 1955.

That was right before the Saugatuck River was filled in, creating Parker Harder Plaza.

At the time of that photo — and ever since there businesses on Main Street — the river lapped up against their back doors.

Just like this:

(Photo/Peter Barlow)

Peter Barlow’s 1947 photo shows the Tally Ho restaurant. It was located — according to this 1950 matchbook — at the corner of State Street (now the Post Road) and Main Street.

That’s probably the site of the noted 1960s-’70s restaurant, West Lake. In modern terms, it’s next to the stark concrete plaza directly opposite Anthropologie (Bedford Square).

The not-to-scale map calls Main Street “Route 57.” Apparently, that’s its official name.

If you’ve got any memories of the Tally Ho — what kind of food it served, the type of customers, what it meant to be a “cocktail lounge” back in the day — click “Comments” below.

19 responses to “Friday Flashback #58

  1. Dan — I think “Route 57” refers to the vertical line just below the first R in Merritt. There’s an arrow pointing to it.

    I love to read these Flashbacks. They show me what I missed not moving here until 1983.

  2. Barbara Sherburne '67

    Note the misspelling of seafood above Cocktail Lounge.

  3. Carl Addison Swanson

    Yep, Westport got blasted with hurricanes, back to back years in the early 50’s which led to the landfill Parker-Harding Plaza. Back then, merchants used to throw their garbage out their back doors. The Leavitt Pavilion area used to be the dump, back when and then a baseball diamond was built there. Dug your cleats in hard enough in the batter’s box, a beer can would pop up.

  4. Well, you did give us some info about the Tally Ho back in 2014, where you said: “West Lake took over the bankrupt Talley-Ho Tavern, which featured a grand piano with lounge singers.”

    What I can add is Tally Ho was a trade name of the Westport Catering Corporation, of the same address (3 Main St) and Theresa Knapp Lightman (1898 – 1982) was the president of that company. She was widowed from Ralph Lightman and possibly living in Westport when she died.

  5. Annnnnd, Rosalyn M. (Lightman) Brown was the daughter of Theresa and Ralph, and she was a 50 year Westport resident, passing away in 2011, Buried in Willowbrook cemetery.

  6. Amazing photo. But thought I’d mention the WestLake resto was around earlier than the 1960s. My family had dinner there on our first night living in Westport in June of 1953. My dad and Mr. Lee hit it off and the restaurant became a favorite.

  7. Linda Dinsmore Tufts

    This was my grandfathers restaurant and served traditional foods, steaks , had its own bakery to make their rooms and bread for the tables. The restaurant was in the front off Main Street then there was the bar area and towards the back was a long with a piano ,after theater dinner or late supper with music. If you need more info let me know

    • Hi Linda, I’m totally enjoying your comments really your family Westport restaurant history. my own grandparents I’m pretty sure were – – when visiting Westport from NYC – if they weren’t regulars they liked the Tally Ho a lot because I remember hearing about it. When I finally get back to their photo 📦 I’m going to make a point to pull out photos marked Westport, CT and see if tally ho is in there. (They socialized and were partners with Herb McCarthy of South Hampton and Billy’s of UES so they seemed to have photos with owners of most restaurant they liked)

  8. I also remember the Westlake way back in 1952, 1953. I belonged to a group of “little girls”, very little, who loved going there for lunch!

  9. Linda Dinsmore Tufts

    Mr. Lee took over the restaurant after a hurricane flooded Main Street. All the extra supplies were in the basement under the restaurant and all was lost and my grandfather was injured and didn’t have enough insurance to ever reopen the Tally Ho. Several off his employees lived upstairs in the apartments. A few years later my grandfather opened The Players Tavern next to the Playhouse and resumed the tradition of the supper club from the Tally Ho. At that time the Play House was summer stock for pre-Broadway .

  10. Awesome info Linda – I never knew the Players Tavern followed the Tally Ho

  11. By the way, the Westport Directory from the mid-50s list Ralph and Theresa Lightman managing the “Compo Beach concession”

  12. Linda Dinsmore Tufts

    I think that Compo Beach maybe after the Players Tavern.because I worked the candy counter there….no I was not of age to work but it was a family run business….then grandpa went to Longshore to run their restaurant and Half Way House where he stayed until the town of Westport bought it. You must realize this is all from memories of a young child and not to sure how long the Players Tavern was open. Thanks for letting me share some memories with you.

  13. Here’s a photo supposedly taken inside the Tally Ho at a dance class graduation dinner. (It’s from the Staples ’55 website and, judging by the ages, must have been taken around 1950):

  14. I believe that the Kawanis held their annual holiday party with Santa in the “lounge” portion of the restaurant and if memory is correct. Santa’s helper was Ralph Brown

  15. Linda D. Parker

    Wonderful memories and information, Linda. I well remember the West Lake restaurant and the Clam Box – family favorite Westport restaurants in the ’50’s!

    • Linda Dinsmore Tufts

      Would love to hear or see any pictures or memories…sorry it took so long to respond but I was on vacation