Friday Flashback #226

This could be one of my favorite “old Westport” photos ever. And not just because it shows the spot where I live today.

Westport Country Playhouse public relations manager Pat Blaufuss found it in the archives. There is no photographer’s credit, but it’s dated 1969.

There’s the Playhouse, midway up the right side of the photo. (Click on or hover over to enlarge). It’s been modernized, but looks pretty much the same.

Saugatuck Congregational Church on the left has not changed much. Neither have the gas stations: the one that is now Quality just east of the church, and the (now) Mobil across the Post Road. The buildings with (among others) Winslow Park Animal Hospital were there then too (lower right).

But the rest of the area is unrecognizable.

The big Victorian at the top was the Pine Knoll Inn. It was demolished in the early 1980s, making way for Playhouse Square and the Playhouse Condominiums behind it.

The long rectangular building with a white facade directly opposite the gas pumps was a car wash. I’m not sure what the white building set back from the Post Road in the entrance to Pine Knoll was, though I dimly recall the original Viva Zapata’s restaurant being somewhere around there.

And the smaller white structure to the immediate right of the Quality (then Tydol, later Getty) gas station, on the Post Road?

Originally a Dairy Queen, in the 1960’s it became the Crest Drive-In. It was a classic hangout for Staples students, a place for guys to show off their cars and girls to get guys to pay for their burgers.

Eventually the Crest gave way to Sam Goody, Alphagraphics and Qdoba. Today it sits as empty as the lot behind it was, that day in 1969 when an unknown photographer took this time capsule shot.

21 responses to “Friday Flashback #226

  1. Great photo, Dan. Thanks. We used to go to the crest drive in for hot dogs with bacon and mustard or pizza. I remember the somewhat bald gentleman who ran it and the other older fellow I believe was called Sam. They were always so nice. When were not going there, we would go to the old arrow, mario’s or chubby at compo Beach by what were then the old locker rooms from s bygone era by the pavilion which still stands.

  2. I think I remember the building in the middle of the parking lot being a hair salon mid 60’s I also believe it has a flat roof and some “childish antics” taking place on that roof.

  3. Great aerial but I just confirmed through a Westport News article that Carroll Reed opened at Playhouse Square in August, 1972. The old mansard roof inn may have lasted a bit longer behind the development but I knew the early 1980s was too late for Playhouse Square because my Mom and sisters worked at Carroll Reed soon after it opened.

  4. India van Voorhees

    The building in the middle of the parking lot was my mother’s restaurant (The House of Buffet) circa 1962. It didn’t last long — one summer, I think.
    I’m STUNNED to see a photo of it!

    • India, I love the name of the restaurant. I’m sorry it didn’t last long. I was curious and googled it—and found a listing from the 1960 Town Crier at 295 East State Street (so I assume that’s it).

      • India van Voorhees

        Ah, 1960. Thanks! We only came up to Westport (from Manhattan) between 1959 and 1965, I think – so I wasn’t sure which year.

  5. one crowd went to Crest, a different one went to Big Top. They bring to mind two different plays/movies: Grease and Hair.

  6. Yes, used to go to the Crest with my first boyfriend, Johnny Polizzio! Wow – he had the cool Thunderbird and all the moves! Great times back in the 60’s.. Pizza burgers were amazing…
    Miss all that..seems like yesterday!.

  7. Guessing many of the cast making their way through the Straw Hat circuit stayed at the Pine Knoll Inn. As well as 1 Beachside Ave. which IS still standing and much improved since it sold in 2003 and again this past December

  8. John (Jack) Wandres

    Was this before or after the Congregational church was moved across the Post Road . . .and made the cover of LIFE Magazine

  9. Richard W. Alley

    The nice guy who ran the Crest was Andy Klein. Last saw him after his retirement fishing aboard the Delmar, a party boat that used to sail daily out of Bridgeport. Nice hearing from my old classmate (Staples 53) , Jack Wandres.

  10. Jill Turner Odice

    Loved the Pine Knoll Flophouse as we called it 😊
    I remember Doris had a horse and I seem to remember Chot Kemper having an airplane?
    Erik Russ lived there during the Open Line days and I stayed in the Cupola for awhile. We had friends stopping by from Players Tavern…
    I remember sending you photos I shot as it was being torn down to make way for your condo…

  11. Great shot.
    My first job at the Crest Drive in. Remember working for Don Manley and Rikki Ball. I think the owner was a guy named Andy from Fairfield. Greasers use to show off their hot rods & bikes,, ,definitely a scene out of Grease!

  12. Peggy Monsarrat

    Spent lots of fun times at the Crest in high school. Andy did the best “ double cheese Mayo also” and then I think he went to the Duchess. Back then we could sit on the hoods of cars and they didn’t dent! High school 1960.

  13. Player’s Tavern to the left of the Playhouse. Saw Richie Havens many times, Peter Tosh, Weather Report, and uncounted nights of dancing there.

  14. My dad was a regular at the Crest back in the 60’s. I grew up hearing lots of stories about that place.
    Many years ago, while watching The Outsider’s, one of my mom’s cousins pointed out Patrick Swayze’s character and said “That’s what your dad looked like back in his day” I still tease my dad about that!

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