Friday Flashback #269

Our very first Friday Flashback — back in August 2016 — featured the Pine Knoll Inn.

That was the long-ago boarding house — and before that, a home owned by the Kemper family (whose tannery and orchard are now the Westport Country Playhouse) — that was torn down in the early 1980s.

Today it’s the site of Playhouse Square.

This was the photo. It was quite a cool looking place:

But now — thanks to James Gray — we’ve got some photos of what the boarding house was like inside.

According to a brochure James sent, it was “lighted by electricity.” It featured “hot and cold water in each bedroom,” and “open sanitary plumbing.”

A boarding house bedroom …

But wait! There was more!

Pine Knoll was “delightfully cool in summer, and having a southerly exposure, is remarkably pleasant in winter. Steam heat, run by Nokol, assures and even temperature at all times.”

… and the dining room.

It was “an ideally located place for those wishing to commute to New York.”

Plus “there are churches of all denominations, public schools, and the Bedford Y.M.C.A., all within five minutes’ walking distance.”

Prices were available “on application.” The telephone number was “Westport 308.”

15 responses to “Friday Flashback #269

  1. Oh, yes. One of the great creepy places in Westport History. In the 70’s it was quite the party house and we were cautioned to never approach it as kids because ‘it is full of hippies’. Pebbles throw from The Players Tavern.

  2. Kristan Hamlin

    It’s a pity that architectural gems like this were permitted to disappear from our Westport landscape. Why not try instead to renovate and preserve homes and buildings that capture the character of a town?

  3. Kristin, 41 Old Road, ‘The Backiel House 1910’ has a preservation award. What I’d really like is to get Bowling Lane, next to the house, changed to Backiel Farms Lane. Bowling Lane was named Bowling Lane because we owned Westport Lanes. I think it was a poor choice of names because we farmed for 50 years. The front of 41 Old Road looks as it did in 1910 when it was built!

    • Jack, Did you meet Allen Funt when he shot a Candid Camera segment there? I remember seeing the plaque at the bowling alley memorializing this part of our Precious TV Heritage.

      • Peter, I was 14 when that segment was filmed, and it had to be kept a super secret, so I wasn’t notified. One of the people who worked for Candid Camera bowled at Westport Lanes, so he’s the one responsible for getting us in TV.

  4. Hard to imagine that as recently as the early 80’s there was still a residential property with a big lawn leading up to the Post Road. Dr. Isenman’s Victorian on the site now occupied by the Wright Street monstrosity is another one I remember. Ever since, our stretch of US -1 has been an uninterrupted wall of businesses, save for the occasional church. Somehow a few other towns, like Darien, avoided this total commercial transformation but, sadly, not Westport.

    • And the old house between the fire station and Terrain. And the old Linxweiler house, now a Homes with Hope property between Fresh Market and McDonald’s.

  5. I’d like to know how that Wright Street monstrosity ever got through zoning!

  6. Gloria Gouveia


    As Zoning Administrator for the the Town in the earlier 80’s, it was my task to inspect every inch of the old mansion to determine the number of existing dwelling units as that was the number of new dwelling units which could be constructed anew.
    The attic was still full of newspapers and other unredeemable junk and detritus. Sunshine peeked in through the walls and roof. Most memorable was one apartment on the ground floor/basement that was so dark I truly couldn’t see my hand in front of my face despite the brilliant sunny day.
    The profusion of cobwebs dwarfed any in Disneyworld’s Haunted House ride.
    In short, the building was far beyond saving. I remember remarking in my report that the only thing keeping the building standing was the termites holding hands.

  7. Jill Turner Odice

    I lived there in a couple of different rooms and the Cupola. We got free rent for the first month after cleaning out one room when an old woman who was quite the Packrat died.
    There were always interesting neighbors, and Chot was quite the character.
    It was very convenient to partying at Players Tavern, being right next door. Living in the Cupola on the top was an adventure, but got old quickly seeing as how there were windows all the way around. I sent Dan a few photos I had taken as it was being torn down, the end of an era…If only those walls could talk!

  8. Bill Strittmatter

    Interesting that houses were allowed to be turned into boarding houses. I would imagine one could do the same with some of the McMansions that have been built in Westport over the years. Wonder if zoning would allow it. Would likely qualify as affordable housing. Maybe a new 8-30g angle. Hmmm.

  9. I, too, grew up with that hippie mythology. In fact, around 1977 my school bus driver was a hippie who lived there. She had the habit of hanging pictures of Hindu deities from the rear view mirror.

  10. This article describes musicians living at Pine Knoll Inn in the late ‘70s:

    “Let’s go to Westport, Connecticut, USA- home of the affluenza NewYork art directors and broadway casting directors, with a few famous actors thrown in— The only other band you may have heard of with it’s core roots in this town was UT—Jaqui and Sally were in our extended social circle back in high school days. How was it possible to be homeless in this suburban wonderland? Was it?? Thanks to one Doris Kemper,ex-rockette,in her 60zz, there was an alternative- get a job washing dishes, and rent a room in her giant cupola-topped former inn gone wrong….”THE Pine Knoll Inn”-…once home to the actors doing summerstock theatre in the heyday of the Westport country playhouse, by the 70zz, it had fallen to the refugees of hard life city. 3/4 of the tenants were on a goverment check, heavily medicated, and ready to ROKK!!!! Thus,”The Kirby Clinic” was born-named after a cocker spaniel belonging to a resident….it was 24/7 madness. The scene was off the hook- the House was located next door to The Players Tavern-playing host to the likes of Muddy Waters and Peter Tosh-and virtually every midsize clubscale touring artist…whenever there was a show, the musicians would come out and party in the relative unsafety of our parking lot.”

    “The Hole Room was on the ground floor of the Clinic. Peter lived there and it had a bathroom. With a drumset crammed in the corner and a couple of amps of dubious origin, our experiments had a fulltime audience, bringing offerings of various sustenance-along with new friends almost daily. This quickly became the refuge for the street people and scenesters of town- safely behind the chainlink fence, you could do as you wished, unless Doris called the police- which rarely happened ( when cars were rolled over and set on fire, apparrently it was within our rights to do so…“

    Do any of Dan’s readers remember the “no wave” band “Ut”? Apparently it’s roots began in Westport. The founders were Jacqui Ham and Sally Young.

  11. Boy this is hard to read! So I guess we can’t blame incoherent writing just on Gen Z bloggers. Actually, seeing that this was from the 70’s, i suspect it wasn’t as much Writing-Under-the-Influence as an attempt to imitate Tom Wolfe. Some chemicals were likely involved, however…

    • Peter: It is difficult to read. I omitted several parts when I copied and pasted. I got the feeling that the author lived quite the life while at the Pine Knoll Inn. He mentioned meeting Pat Metheny in the parking lot after Pat performed at Players Tavern, among other artists. It must have been quite the scene!