Street Spotlight: High Point Road

Today, “06880” introduces a new feature. “Street Spotlight” does just that: It shines a light on a Westport road, from a resident’s point of view.

What makes your street special? Do you have unique traditions? Does one particular person, family or physical feature bring people together? Has everyone gone through an experience that bonded residents tightly?

“Street Spotlight” will run irregularly — whenever we get an interesting submission. Here’s your chance to show off your road, lane, drive, circle or court to the entire “06880” community. Send info and photos to Happy trails!

High Point Road has a couple of claims to fame.

It’s supposedly the longest private dead-end street in town. Rod Serling once lived (and wrote “Twilight Zone” episodes) there.

High Point Road (red balloon) runs parallel to — and between — North Avenue and Bayberry Lane. Unlike those streets, it’s a dead end. The only way in or out is Long Lots Road.

But at its heart, mile-long, winding, hilly 70-home High Point is a true community.

In past years, there was a formal association. Members paid dues, elected officers, even produced newsletters and lists of every family (with kids and phone numbers).

A few years ago, someone made a map of all the homes — and listed every family that ever lived in them. This is a partial view of that map.

The association no longer exists. But there are still annual street gatherings for kids and adults. It’s a great trick-or-treating street. Every Thanksgiving, residents walk together.

High Point has an interesting history. It was developed out of woods and fields in the mid-1950s — around the same time Staples High School was being built, just behind its western hill. Most early homeowners did not yet have kids in high school. But as they grew up, the athletic fields behind the fence became a huge draw.

On the other (eastern) side, Muddy Brook flows through High Pointers’ back yards.

Ann Gill was among the first residents. Her death in December marked the end of the original homeowners. Until a couple of years ago, several families remained from those 1950s days.

Some of their houses still stand. The architecture was an eclectic mix: Cape Cods, colonials, modern, and some custom homes.

High Point Road homes are built in a variety of styles. This view looks west. Staples High School’s field hockey field is just beyond the homes on the right.

Most have been renovated. About 1/3 of the houses are large replacements of teardowns.

I grew up on High Point. It was a wonderful road — filled with boys and girls my age. We rode our bikes all the way to the cul-de-sac at the end, where we played all the games kids played back then.

The cul-de-sac. We called it “the turnaround,” and played there often.

We had block parties at Staples and on then-vacant lots, and carol sings. Our fathers rented a bus for a trip to Yankee Stadium; our mothers had their own garden club.

In this 1965 aerial view, Staples High School is on the left. An arrow points to High Point Road — and the house I grew up in.

A lot has changed. Kids no longer walk from High Point to nearby schools: Burr Farms Elementary School (it no longer exists), Long Lots (it was a junior high back in the day) or Staples. Then again, they no longer walk to school anywhere in Westport.

Families with pools no longer open them up to every kid on the road one day a week. (There are more pools — and much more liability).

But the neighborly vibe of High Point Road continues. The holiday traditions remain.

And it’s still — I think — the longest private dead-end road in Westport.

(Hat tip: Amy Saperstein. To nominate your road for a “Street Spotlight,” send info and photos to

Former and present High Point Road residents reunite on their street. (From left): Ursula Malizia grew up on High Point, lives there now and teaches at Kings Highway Elementary; Anne Delorier, Aimee Latzman, Carlotta McClaran Simunovic, Amy Saperstein, Shikha Sharma, Anna Inglese and Jen Gorin.

43 responses to “Street Spotlight: High Point Road

  1. Dennis Jackson

    So you must have known the DeHarts and the
    Wildes.      John DeHart was my college roommate.
    The Nesbitts were there when I knew them in HS,
    but no one else.      Are the Sloats the “Sam Sloats” of coins
    and stamps?      

    • I did know the DeHarts. They were the family that opened their pool every Monday to kids on the entire street. That would never happen today, if only for liability reasons.

      Pam Wilde was one of my oldest and best friends growing up. Her sister Zazel is the model on the back of the Doors’ “Strange Days” album, standing in the doorway with the juggler. We always thought that was very cool.

      And the Sloats are the same as Sam Sloat’s business. Robert Sloat – a year older than I — owns a lot of commercial real estate in town, and lives in the old Schlaet estate.

      And of course the Jackson family lived on North Avenue, where we cut through on our way from High Point to Burr Farms.

  2. I grew up at #9 High Point, just down the street from Bob FInk and cater corner from the Serlings (later the Leffs) and across from the Sternbachs (lqter the Gambaccinis) and up from John Zurich. And worked as a kid for Bob Sloat’s dad and Joe Ziehl’s dad, at the end of the street. Pretty idyllic times. Walked to Long Lots Jr. High and Staples. Those were the days. Now our old house is scraped and replaced by a McMansion, of course.

  3. Mark Yurkiw

    Love this new feature! over time it will need to be archived at the WHS.
    Things like the hand made map are a treasure

  4. Fred Cantor

    Holy cow! I never realized it was a mile long. Does anyone know why the developer opted to make it a private road?

  5. Richard Fogel

    Is this the street where a neighbor posted a front lawn banner God Bless Donald Trump??? Thank you.

    • Yes. What does that have to do with anything?

      • Richard Fogel

        It helped me identify the street name. How many streets in town have a large sign that reads God Bless ?????????? in front of a residential home? So when you ask me what does that have to do with anything, it has to do with identity to a street. I guess i am the only one who thinks it stands out.

        • It’s a dead-end road, Richard. Not much traffic except for residents. So it’s not as if a ton of people saw it, other than neighbors.

    • Bob Stalling

      How dare they!
      I call for an investigation!

  6. Jill Denowitz

    This was a great road to grow up on, My house was the last on the block, #71. It has not been torn down, but has changed hands several times since my parents moved to saugatuck shores in 1990. We had to walk to Long Lots Jr High and Staples, but had a bus stop in the cul de sac to take us to Burr Farms El.

  7. Lewis Grossman

    Jill’s brother, Lewis, here. High Point Road was, indeed, a great road to grow up on. As Jill mentioned, we lived on the cul-de-sac, which we called “the circle.” It was a great play area, rarely interrupted by traffic. A fence on the Richards’/Morleys’ side of the circle served as the perfect home run fence for Wiffle ball games. So many kids lived on High Point Road in my day that they probably filled about half of a Burr Farms bus. Attractions lay a short walk from our house in every direction. The Staples athletic fields.The Nike missile site with its empty silos and ominous “No Trespassing” signs. Woody Lane and its own wonderful community. Christie’s Country Store, at Woody Lane’s intersection with Cross Highway. Bayberry Lane was a bit more difficult to access–it was on the other side of a skunk-cabbage filled swamp–but I often made the trek anyway, reaching my friends’ houses with sneakers covered by orbs of mud.

    Last month, my Mom accompanied me on my once-every-few-years nostalgic journey down High Point Road. I had trouble getting my bearings for the first two-thirds of the trip–too many new houses, absent trees, etc. But once we hit the straightaway near the end of the street (starting around the houses I knew as the Robins’ and the Gills’) the view was largely unchanged, and we could almost imagine it was 1975.The saddest absence for me was my Dutch-elm-disease-resistant elm tree, which we planted on Earth Day in 1970 and which flourished for decades, but is now a mere stump, like its counterpart in Shel Silverstein’s The Giving Tree. Fortunately, I remain more sprightly than the old man sitting on the stump in that book’s final pages.

  8. Amy Saperstein

    Great article Dan!
    Please note that lots of kids from High Point still walk to Long Lots, Bedford and Staples! Hopefully, that will be able to continue as that is a high light of the warm weather!!!

  9. A. Darcy Sledge

    I also read somewhere that it is the longest cul de sac as well as the longest private road !

  10. Jalna Jaeger

    I knew several people who lived there, Kathy Smith, David Nesbit,John Bresnahan, and you Dan. I used to cut through Staples field and someone’s back yard and walk home to North Maple Ave along Highpoint rd.

  11. Jalna Jaeger

    I forgot the Bailins and the Zurichs!

  12. High Point road was a great street and we had those great block parties at the high school.. I still remember doing the egg toss with Scott Guthman!!
    Great story, Dan.

  13. Chris Frey

    We lived at 69 High Point Road from 1970 to 1975. At the end of the road, our back yard was a well used cut through the took one up to the football field. During one particularly nasty infestation of gypsy moths, my mom would leave light walking sticks so that travelers could wave them in front of them to break up all of the webbing they wove through the path.

    The No Trespassing signs at the Nike site did nothing to deter my friends and I from frequent forays around the base, checking out the jeeps and other vehicles parked there in the early 70s.

    The bike ride to Long Lots was quick, and we knew where we could cut through the “swamp” to minimize muck and mud. A few of my friends would meet at night and climb the affixed ladder behind the cafeteria and walk along the tops of the covered walkways while smoking what was then very weak Mexican

    And on a healthier note, Doug Kaufman (also a HP resident) and I played badminton in state and regional tournaments and did quite well. Dad actually made a regulation court in our small backyard where we practiced innumerable days after school.

    Cut a lot of lawns back in the day and bought my first car with those earnings.

    Good memories, good neighborhood. And Dan, I remember the mailbox with the “Woog” name on it.

    • John Kelley

      My family was the original owners of 69 High Point Road. It was built in 1955 by a Mr. Zullo, whose brother was the mayor of Norwalk. It was painted grey with white shutters. It cost $42,000 and when we moved in 1962, it sold for $42,000 after being on the market for a year. Any father built a brick barbecue in back. Staples was not yet built but there were woods with lions, and tigers and Indians (or so we thought) so we never ventured into them very far. I started elementary school in 2nd grade at Greens Farms School (but at Greens Farms Congregational Church due to overcrowding). The following year we were at GFS proper but my sister was in 1st grade at Saugatuck Congregational church. In 1957, we were supposed to be at Burr Farms School but it was not yet finished so GFS was in double session until December when Burr Farms was finally opened. Last time I saw the house the whole character was changed with an addition built over the North side and a u-shped driveway installed snd it no longer resembled a ranch.

      • We had a ping pong table in the basement to the right, and a “party” room to the left in the basement. The bedroom on the Staples side had built in shelves, and when my brother and I visited and knocked in the door for during my Class of ’76 40th high school reunion, his cast iron ice truck and horse, as well as his cast iron cannon were still on those shelves. Yeah, the built up room over the garage was different, as well as quite a bit of clearing in the back yard, but it was better than a tear down!

    • Lewis Grossman

      Chris, we were your neighbors in #71 during those years. I have dim memories of your badminton court in the backyard and you practicing with Doug Kaufman. (I was buddies with his brother, Ted.) I have very distinct memories of the peculiar hell that was walking up “the path” to Staples during caterpillar web-spinning season with my French horn in one hand, my books in the other, and my face thus totally unprotected.

  14. Carl Leaman

    I don’t think its a private road.

  15. Peter Gambaccini

    We only moved in there, at #8, after my sophomore year of high school in 1966 (I guess) after having lived elsewhere in town. I tried cutting through someone’s backyard to get to Staples once and was told not to do it again. Obviously I was misinformed. Nuts. So I was more dependent on a car than I wanted to be. Anyway, I loved our big sylvan space there and the house that a subsequent owner plowed under (a common Westport story). My greatest achievement there, despite discouraging words from absolutely everyone, was managing to grow cucumbers on a mound on the “south lawn.” I also fondly remember, before the days of electric fences, how much fun our dog had running around with the other High Point pooches.

  16. Chris Weissman

    I grew up on High Point Rd in the late 70s. Lived at #14 (where Rod Serling lived). Used to walk to Long Lots and Staples rain or shine. It was a great street to grow up on. Nice families and a real sense of community. Thanks for the spotlight Dan

    • Craig B. Librett

      Hi Chris and everyone. This is Craig Librett. We were the owners of No. 14 (Rod Serling’s house) right after the Weissmans. Spent my entire teen years there. Loved cutting through (who’s?) driveway to get through to Staples. Did it every morning, until I got a car. Some of my best memories are from High Point.

  17. Nancy Powers Conklin

    And, back in the 60s, High Point Road had one hell of a mailman!

    • The best mailman of all time: George “Nooky” Powers. Fantastic athlete at Staples; World War II vet; wonderful, caring, trustworthy, friendly and great. My dad loved him, and they had a very special friendship. High Point Road was very lucky, for sure!

  18. Juliana Fulbright

    We went sometimes to Bob house and got stoned and liquored up the only time I threw up for having both.. Haven’t had pot much since those days . Kim Cooper and Mark Owades who I haven’t seen in a couple of years

    lived there for years, same house. They did A beautiful job inside which I was in, from the beginning . It’s gone now but it was fun, went to many parties there and I loved it and them. She and Hubby are down in Florida after living through some awful fires in Cali.

  19. Pam Gaherin Watson

    oh my..I loved High Point Road though I was the oldest sister. All my younger sisters really grew up there. it broke my heart when our house was torn down. I remember the Yale Medical
    School dates I brought home there..and the 1964 mustang my Dad bought me when I graduated from nursing school..I first drove it up and down high point road. Everyone in our family loved High Point was a special piece of Americana! Pam Gaherin Watson

  20. Sabrina Weinstock-Dubbs

    I lived at #36 High Point right next to your family Dan. Your parents invited us to their pool all the time. They were the nicest people. Great memories growing up there! Walked to Long Lots, and cut through to Staples. Thanks Dan.

    • Those were indeed the days. Thanks for being a great neighbor! (And right next to you on the other side were the Gaherins — just as they’re next to you in the Comments section here!).

  21. Nancy Powers Conklin

    Thank you for the kind words, Dan. I know what a special road High Point was!

  22. Katharine Murray

    We live on High Point now and even though some of the houses have changed since we originally moved here it really is a great community. It has become a “destination” for Halloween which is a lot of fun. Many kids do still walk to school – Long Lots, Bedford and Staples. Such a great benefit to living so close to the school. We absolutely love High Point!

  23. Fred Cantor

    Since there is a plaque commemorating F. Scott Fitzgerald’s having lived on South Compo, has High Point Road ever considered doing something similar re Rod Serling? I gather that the house he lived in has been torn down but, nevertheless, he lived on this street while conceiving and/or writing quintessential stories about mid-20th Century American life in general and suburbia in particular.

    As many “06880” readers know, one of Serling’s most famous Twilight Zone episodes, “A Stop At Willoughby,” is about a Westport commuter.

    And, who knows? Perhaps Serling even had an inspiration for one or more of his stories seeing the neighborhood kids go by on High Point.

    In any event, Serling clearly spent considerably more time in Westport than Fitzgerald did.

  24. Tom Croarkin

    I lived nearby on Moss Ledge Road. When I was in High School in the early 70’s we would walk up Moss Ledge, cut through the Connelly’s yard to go through the Lint’s yard onto High Point and then walk to the Goldbergs (?) and cut through into the Athletic Fields at Staples. It was a great short cut not just because it saved time but because all the cut through families seemed to be OK with it.

    I have especially great memories of the Milberg and Kaufman families who lived on High Point during that time. And where would we be without the Woog family. Great place! Great people!

    • And I remember when the Croarkins moved to Westport, from Chicago. A great addition to Westport.

      Tom, you probably know that all of Moss Ledge used to be one estate. The Lane family (including Staples football coach Paul, and hamburger restaurant owner chubby) owned that entire property. We used to cut through there too, on our way from High Point to points west. All those houses were built in the mid ’60s on.

  25. Jaime Bairaktaris

    Such a cool story and idea.

  26. Anne Delorier

    Hi Dan! This is Anne Chaney- now anne delorier (Staples class of ‘95)… I now live with my husband and 3 kids on High point Road! We live at #67 down at the end of the street. So fun to read you also lived on our road and learn some of the fun history of our favorite street in town! I have one concern about something you wrote… There is talk of redistricting our kids to Coleytown middle school… which would be very upsetting considering Bedford is literally in our backyard! You stated that the kids don’t walk to school anymore… and I’m sure the numbers have decreased over the years, but if you visit high point road between 3-4pm I think you’d be happy to see many clusters of neighborhood kids (including kids from neighboring streets like Sprucewood) walking and riding home from long lots, Bedford and Staples… my kids included! My main point when writing letters to the BOE and the other powers that be, is that our kids walk to school and it seems silly, unhealthy, and logistically wrong to put them on a bus… after all, it is one of the main reasons we bought our home on this fabulous street. I used to ride my bike to Bedford- now Saugatuck… it’s one of my fondest memories of growing up in Westport! Anyway, the redistricting worries me, and when I read your post, it added to my concern that the BOE might actually think no one walks to school anymore. Which would be very inaccurate. Long lots needs to go to Bedford. Hope you are well. Thanks for listening… Anne Delorier High Point Road Super Fan

    Sent from my iPhone


    • Thanks, Anne — great to know kids still walk to school. I wrote that because while visiting my mother from time to time, I’d see school buses go up and down the road. I should have checked with the experts!

  27. Vicky Powers

    Thanks for the great article! We’ve lived at 33 High Point for about 8 years, and were told that years ago our front yard pond was much larger and deeper and that all the neighborhood kids used to swim in it! I believe you grew up across the street from us – was it really he neighborhood swimming hole? My husband tried to clean out some branches during our first summer here and literally got stuck in the muck at the bottom!

    • Yes, I grew up at #34 (and remember your house being built!). It was NEVER a “swimming hole.” In fact, I’ve never seen anyone swim there. Yes, it was bigger and less murky — but never a real pond. I did once pull a neighborhood kid out of there who fell in — but that’s the closest anyone ever got to “swimming.” Hope that helps!

  28. The Kaufman Family (Art, Ruth, Ken, Ron, Douglas, Ted, Cathy) lived at 26 High Point Road from the early 1960’s until the mid-70’s.

    The house cost $14,000 when purchased and lists for close to $1M on Zillow. Enjoyed a tour on Zillow and smiled to see extensive interior renovations but not a single change to the exterior or landscaping of the house.

    The neighborhood was absolutely incredible for kids: front and backyards, sporadically available swimming pools, bicycles and skateboards (with metal wheels that rankled your ankles), lots of dogs, a big yellow school bus. Cathy, Michael, and Mary-Ann ten Kate lived across the street. (Cathy now leads development for a city-wide homeless shelter in New London.)

    Dan Woog is right about the pond at #34 never being a swimming hole. It was good for ducks and for losing balls in occasionally, but never looked inviting for a swim.

    The walk or bicycle ride to Long Lots was down and back up the BIG hill (which today looks like gentle slope). And the path to Staples was legendary, took you from High Point right to the corner of the big athletic field.

    Thanks to everyone’s parents who paid us kids to babysit, shovel snow, rake leaves, mow lawns, and deliver newspapers (it was a good route to have for getting tips).

    Thanks for this great article, Dan. What a gift!