High Point Road, One Brick At A Time

My parents moved to Westport in March of 1956. A blizzard prevented the truck from going up the driveway. The movers hauled just one bed inside, so my parents spent their first night in a barren bedroom.

My mother died in that same room almost a year ago.

This winter, my sisters and I sold her house. That ended 60 years of the Woog family on High Point Road.

It was quite a run.

I guess that qualified me for an email the other day from current High Point residents. The Westport Historical Society is building a Brickwalk, and my old street is going all in.

A special stone will say “High Point — The Best Road in Town,” with residents adding their own bricks engraved with the year they moved in.

I was honored to be asked. When she died, my mother had lived on High Point longer than anyone else.

The Woog brick will say “1956-2016.” But there’s no way that small rectangle can encompass 6 decades of life there.

High Point is the longest cul-de-sac road in town. Call me biased, but it’s also the best.

I was so fortunate to have grown up where and when I did. My parents — both in their early 30s — had no idea what High Point would become when they moved out of my grandparents’ house in New Rochelle, and up to this much smaller town.

Rod Serling and his family celebrating Christmas, at their High Point Road home.

They had a few friends here — including my father’s Antioch College pal, an already famous writer named Rod Serling. He and his wife Carol had just moved to High Point. There were plenty of building lots available, so my parents bought one.

The price — for an acre of land, and a new house — was $27,000.

As I grew up, so did High Point. My parents were among the first dozen or so families. Today there are 70.

I watched woods and fields turn into homes. Nearly each was unique, with its own design.

And nearly each had a kid my age.

My childhood — at least, my memory of it — was filled with endless days of bike riding, “hacking around,” and kickball at the cul-de-sac (we called it “the turnaround”).

At dinnertime in spring and summer, we’d wander into someone’s house. Someone’s mother would feed us. Then it was back outside, for more games.

When my parents chose High Point, they were only vaguely aware that the new high school being built on North Avenue was, basically, in the back yard of our neighbors across the street.

Having Staples so near was a formative experience. My friends and I played baseball, touch football and other sports on the high school fields. We watched as many football, basketball and baseball games as we could, in awe of the guys just a few years older. Once, we snuck into a dance in the cafeteria. (We did not last long.)

This aerial view from 1965 shows the separate buildings of Staples High School. Behind the athletic fields is High Point Road. My parents’ house is shown with an arrow.

There were enough kids on High Point to have an entire bus to ourselves (with, it should be noted, only 3 or 4 bus stops on the entire road).

But by 5th grade, my friends and I were independent enough to walk through Staples, across North Avenue and past Rippe’s farm, on our way to Burr Farms Elementary School.

We talked about nothing, and everything, on our way there and back. It was a suburban version of “Stand By Me,” and to this day I cherish those times.

The young families on our street grew up together. There were block parties every fall, carol sings at Christmas.

Every summer Saturday, Ray the Good Humor man made his rounds. High Point Road probably put his kids through college.

Spring and summer were also when — every Monday — one family opened their pool to the entire street. With 40 boys cannonballing, racing around the slippery deck and throwing balls at 40 girls’ heads, I’m amazed we all lived to tell the tale. I can’t imagine any family doing that today.

From the front, it was an average home on a wonderful road …

But that was High Point Road, back in the day. It was not all perfect, of course. Some of the older kids were a bit “Lord of the Flies”-ish (and the amount of misinformation they taught us about sex was staggering).

Behind closed doors, there was the same bad stuff that goes on anywhere (and everywhere).

But I would not have traded growing up on High Point Road for any place. As much as any street could, it formed me and made me who I am today.

… but the back yard was beautiful.

High Point Road has changed, of course. Many original houses are gone, replaced by much larger ones that could be on any Westport street. There are plenty of kids there now, but each has his or her personal bus stop. And I don’t think I’ve seen any gang of kids riding bikes since, well, we did it.

Still, it’s a wonderful road. The “new” residents have kept that neighborhood feel. There are social events. And they always welcomed — and looked out for — my mother.

Of course, you can’t put any of that on a brick.

So ours will just proudly say: “The Woog Family. Jim, Jo, Dan, Sue, Laurie. 1956-2016.”

And that says it all.

(Westport Historical Society bricks are available in sizes 4×8 and 8×8. They can include a custom logo, with a family row of 5 bricks for the price of 4. For more information, click here.)

58 responses to “High Point Road, One Brick At A Time

  1. Adam Vengrow

    awesome reflection, thanks for sharing, those were special times many can relate to, congrats on a great history

  2. Jill Grossman Denowitz

    Great story! As another former high point roader(?1971-1993), this was a nice memory. Will look into adding a brick with our name to the special area of the brick wall!

  3. Dorothy Abrams


  4. When I grew up on Quintard Place in the 50s and 60s, High Point Road was a regular part of my life. As your mailman for most of his 30 years with the Post Office, my father shared many stories of many of his favorite customers. No one road on his route contained more of those than High Point. He would have been so pleased by your story Dan.

    • Thanks, Diana. George “Nookie” Powers was definitely an important part of High Point Road. He and my dad shared a long and special friendship. I’m glad we’re still in touch, carrying on that wonderful relationship!

  5. Such a lovely post Dan. Thank you for writing it.

  6. Jonathan Maddock

    Thanks for the beautiful reminiscence of the past. I enjoy similar remembrances of my neighborhood (Wake Robin/River Oaks roads off of Greens Farms Road).
    I share your memory of Ray the Good Humor Man. We would beg him to do slight-of-hand tricks. He always could pull a quarter out of some one’s ear.

  7. Bobbie Herman

    What a beautiful tribute!

  8. Charles Halper

    An especially lovely piece today, Dan. We came in 1960 and moved to Bayberry lane in 1961. Nostalgia.-Roe and Chuck Halper

  9. Great memories growing up on High Point. My favorite was the egg toss at the block parties held at Staples. Scott Guthman was a great partner in those!! And all those pool hopping teenagers in the middle of the night. Only you know who you were!!

    • Michael Pettee (Saint Paul, MN)

      Susie, pool hopping is exactly what I was thinking about as I read Dan’s piece!

  10. Susan Holden

    Dan, That was a wonderful piece and tribute to your childhood and your lovely parents! I had the pleasure of getting to know them a bit when I owned my jewelry store when we first moved to Westport! One of your sisters was getting married and your mom and she came in to get a pair;) I used to tease ur mom about quitting smoking! She was a spunky one;) Always had a good comeback and smiled through her delivery! Your dad was so sweet! He reminded me of my dad. Easy, warm and a perfect match for your mother;)

    Thank u for the trip down memory lane and thank you for writing ur wonderful blog!

    I’m not sure how you do it, but I’m sure glad you do!

    Warm regards, Susan

    Susan R. Holden Realtor, ABR Douglas Elliman Real Estate Licensed in CT & NY Westport, CT. 06880

    Cell: 203-209-2223 Email: susanrholden@gmail.com


  11. Wonderful memories Dan! What did you think of the nearby Nike site while growing up?

    • Thanks, Jim — and funny you should mention the Nike Site. I thought of including that, but the piece was getting a bit long. I remember the abandoned silos, where my friends and I would play. We never gave a second thought to the missiles that had been there only a few years earlier. Really spooky in retrospect.

      And of course in later years, when I was a high school student, the abandoned barracks were, as legal experts might say, “an attractive nuisance.” If only those old walls could talk!

  12. Scott Brodie

    Dan, What a lovely reminiscence. Rather reminds me of my own elegiac 06880 note about growing up on Burr Farms Road from a few years ago — also triggered by the death of a parent. Your note raises the question of whether my mother might well be the record holder for residents of Burr Farms Road — we started construction of the house where my mother still lives in September of 1954, and moved in the following Spring.

  13. Daniel Souza

    What a wonderful story! Thank you for the vivid vignettes of how a boy grew up on a street that made him who he is.

  14. Dan, a fine historical memoir…truly fine. ,Thank you.

  15. Michael Calise

    Great story Dan! I see much of what you speak throughout Westport and every “turnaround” even if there is no cul-de-sac has it’s memories

  16. How beautifully put, Dan.

    Thank you for sharing it and for making me feel more like a neighbor on High Point rather than an obscure reader of a blog. I got the atmosphere and comfort of that time, almost hearing the riotous voices of your pals/extended family throughout the neighborhood. What a wonderful place (and time) to raise a family.

    Your gift is an endearing one and an inspiration to anyone who loves words.

  17. Audrey Doniger

    Love this story Dan…I remember the old High Point Rd very well..all of my children had play dates on said road (one of them was your sister Laurie)…now I find myself as the only “old member”) of my street,in the only original house bought from The Backalenicks aimost 60 years ago…it was very much like High Point but on a much,much smaller scale….thanks for the nostalgia with my a.m.coffee…p.s.as of now,I’m planning to remain as the little old lady at the end of the road…..

  18. John F. (J-period) Wandres

    Thank you for making me cry, for a time gone by.

  19. Joyce Bottone

    What a great morning read. Thanks for sharing those beautiful memories. I was just trying to remember the name of that farm on North Ave (Rippe’s). Wasn’t that the same family on the Post Road, near Fortunas? I used to got there all the time with my folks, and Wakeman, to get fresh veggies!

    Having grown up on Bayberry, in the late 60’s-70’s, we too wandered the streets on our bicycles, the same way. I am always amazed, looking back, how I’d venture down the windy road to hangout with my best friend on Meeker Road, or how I’d weave through backroads to get to Newtown Turnpike. Did I ever let my kids do that? Yup! They were the lucky ones, when they were young, who resorted to sidewalks, one amenities when you live near a school. And “yes” thankfully when they were a little older we let a group of them ride to Compo or down to Saugetuck school to throw the frisbee/play kick ball.. The older siblings watched the younger ones. That community feel. Mommy taxi service didn’t kick in until they were lucky enough to go to Coleytown Middle School, which was cross town. Boy do I miss those days of hearing every detail of what happened through the course of their days.

    Just a last minute thought, as I ramble, sorry! We donated two brick, in the memory of our families, when they were making the walk outside the new library – and unfortunately, those are barely legiable, now! Still a beautiful thought. Have a great day everyone!

  20. Bill Boyd (Staples 1966)

    Another great story Dan…I was friends with Mike Harris of your road. It still amazes me how long the road is! And your description of the comraderie …it must have been a great place to grow up!

  21. This really did feel like ‘Stand By Me.’ My daughter’s best friend growing up lived on High Point, plus one of my teacher friends grew up on High Point and we’d visit her parents there. I always enjoyed the neighborhood vibe!

  22. Becki Whittington

    Dan – did you know Kathy Zurich? Her family lived on High Point Road. She was in my class (67) and someone thought that she had passed. Do you know? I also dated Carter Brown – also on the same street.

    • Hi Becky,

      Sure — the Zurichs lived at the beginning of High Point. I’ll send you John Zurich’s email privately. And yes, Carter Brown lived there too, for sure.

  23. Susan Hopkins

    One of your most moving pieces, Dan ….

  24. Very wonderful blog today Dan….that is a long run! Many of us westporters of that generation, myself included can relate to this long walks to elementary school and this “stand by me” moments. I am grateful to have had my share… forward we all go.

  25. Linda Parker

    Thanks, Dan – such a wonderful portrait of the life and times of the Woog family on High Point Road…

  26. Linda Parker

    Well, I have to say Westport was the best home town ever – won ‘t forget Sterling Drive, Old Road , Mayflower Parkway, and finally, Wilton Road. Great memories! The TV series? Sigh… I watch it but I’m disappointed

  27. Oh, golly, Dan — Doug Davidoff here. Checking in for on #20 High Point — our house still extant though surrounded by tear downs and replacements. I have so much to add … later.

    I support all the memories of the community on High Point Road — Schine, Zurich, Kessler, Gambacini, Bernard, Weisskopf, Kaufman, Woog, Calby, Morley, among others.

    Three generations of Davidoffs lived at #20 from about 1964 or 1965 to o about 1980. My paternal grandparents, Bernard and Mildred Davidoff, purchased #20 with its spectacular woods-enclosed swimming pool and patio. My parents purchased the house from Mildred after Bernie died in 1967 to keep the swimming pool in the family.

    I did not realize until recent years how important our pool was in healing our extended Davidoff family after Bernie’s death and even more so in the wake of a 1964 auto accident on the New Jersey Turnpike near the Delaware Memorial Bridge took the lives of my six-year-old Davidoff cousin, Adam, and my 29-year-old aunt, Mary “Rusty” Miller Davidoff. My Uncle Paul Davidoff remarried. With his new wife, Linda Greenberg Davidoff (later, Stone Davidoff), they settled in Larchmont, New York, with my two surviving cousins, Susan and Carla Nan. Two more cousins followed, Daniel and Thomas. Many people on High Point Road will recall how our pool was a neighborhood center. I did know until just a few years ago how critical the beauty and recreational value of the property was in restoring fun and normalcy to my family after the tragedy of the 1964 auto accident and the untimely death of my grandfather. Endless games of “Marco Polo” contributed to this!

    I treasure my relationships with my uncle and both of my aunts. Paul and Linda, now both long dead, are models for for me because of their advocacy in city planning, correcting housing patterns in the inequality of New York’s tri-state suburbs (notably, the “Mount Laurel” housing policies in New Jersey ordered and recently reaffirmed by that state’s Supreme Court), and Linda’s later advocacy on behalf of city and national parks inside the City of New York. All this — aided and abetted by that wonderful swimming pool and home at 20 High Point Road. It was a neighborhood center but a family treasure that worked miracles

  28. Carissa Baker

    Dan, how very sweet your memories are! We were so blessed. Thank you, dear friend, for sharing them.

  29. Nancy Powers Conklin

    What a great blog entry, Dan! It brought back so many memories of our own neighborhood on Quintard Place and playing with all the kids on our street. And, Ray the Good Humor guy came to us too. If I remember correctly, I think he told us he had 10 or 12 kids! Whether that was true or not, who knows?? We were just kids and believed everything the Good Humor man told us. And, he did the magic tricks for us too! What great memories!! Thank you!

    • Thank YOU, Nancy! The Powers family — just across the Post Road on Quintard (off South Maple) — helped make Westport great. Our whole family — especially my father — loved your dad!

  30. Dan, what a moving memory you have shared. We lived around the corner on Long Lots Road. I do remember your lovely mother who I know you must miss. May blessings be on you!

  31. Wish we could recreate an episode of …The Twilight Zone…taking us all back to simpler and more carefree times. Thanks for the walk down memory lane Dan.

  32. Great piece Dan! I do remember those block parties, the bus, walking to Staples (through people’s yards), biking up and down the street with the Gaherins, Nesbitts, Wendy Gill, the Wolfs…! And the neighborhood open pool days… wow, that would never happen now. Was it the deHarts? Kleins? Sad to say good-bye to the house. Mom was there a really long time and she still made friends with new neighbors.

  33. Jack Whittle

    Great piece Dan – you really captured the feelings I share with you about growing up in Westport, on a long dead end street with an ample supply of like-aged kids – it sounds idyllic and it definitely was. Meet you in the turn-around after dinner . . .

    Of course, I grew up at the end of Woody Lane, the second-longest dead end street in Westport (second only to High Point) with a short cut to High Point running from our back yard to the Grossman’s on High Point.

    • Thanks, Jack! Can you imagine if our roads had been connected!

    • Jack Whittle

      The Woody Lane Gang was pretty good group of kids (and we had far fewer houses than High Point given our 2 acre zoning) – when I was growing up we had these kids within the same 5 year age window:

      Tracy (Jennifer, Laurie and Todd)
      Floch (Neil, Lisa, Craig and Jeff)
      Clouser (Karen, Karla and Stacey)
      Sirkin (Neil, Brad and Sam)
      Simonton (Scott and Bob)
      Schwartz (Ken and Peter)
      Whittle (Liz, Jack and Jennifer

  34. Barbara Sherburne '67

    Lovely story, Dan, and a beautiful house and home. It was probably a little bit difficult to sell the old homestead, but what a remarkably long time your family owned it. You were very lucky indeed.

  35. J. Scott Broder

    Beautiful commentary and reminiscing of the old way of life in the 50’s and 60’s.
    Kudos to you and your family❗️

  36. Again, you out-did yourself, Dan – a marvelous piece that brings out the old Westport kid in all of us. Of course I’d claim the Rocky Ridge/Nappa Drive neighborhood as the best (good thing there weren’t interneighborhood leagues back then for Flashlight Tag, Whiffleball or Capture the Flag; we’d have won them all and still been home before the 5 o’clock whistle blew) but equally enjoyable to those great memories of our ’60s-’70s Westport is seeing so many familiar names replying to this article. You struck a chord with all of us, Dan, so thanks for another wonderful post!

  37. Scott Guthman

    Great article Dan. Having the high school ” in our backyard” was a treat. I remember, while practicing on the Staples baseball team, volunteering to go retrieve baseballs that were hit over the left field fence during batting practices. Coach Kelly was more than enthusiastic about allowing me to venture into the woods for a half hour or so, because I always managed to return with a many perfectly good lost balls. What I would actually be doing during the break from practice was to get a snack and a swim in my parents pool, grab some balls that were previously found on one of my walks to or from school, and return in time to take some swings and shag some fly balls. Utopia!

    • Love it, Scott! The Guthmans were great neighbors. I remember so well your sister Pam’s 6th grade graduation party at your pool. And speaking of Coach Kelley: One day in the spring of senior year, he took our entire gym class over to my parents’ pool. Somehow I can’t imagine that happening today — and not just because there is now a pool on the Staples campus!

  38. Eileen McManus

    Once upon a time . . beautifully captured, Dan! It was a great time to be a kid.

  39. Great story. One of the wonderful things about growing up in the 50’s and 60’s was the large number of kids in every neighborhood. There was always something to do outside. We also had Ray the Good Humor Man. I think he hit Terhune Drive multiple times every week!

  40. Maryann Gaherin Heller

    Danny, what a great article, thank you! My family loved our years on High Point. My father’s very favorite memory was shortly after moving in, Lori walked onto our back porch, introduced herself, and proceeded to tell him all about her! She must have been 4 years old! He thought she was the cutest thing ever : ) I babysat Lori, later on at your cool house where your room upstairs was off limits! Your wonderful pool that my sisters and I often pool-hopped in. (Amongst others..Thank you Kleins & Davidoffs) My sister Pegeen would throw me in so she could “rescue” me…Our dogs Taffy and Cindy. Our mothers thought we should switch dogs as our Cindy mirrored your black and white house and your Taffy our auburn one. They were off leash always, playing in the woods and the yards, and miraculously nobody got bitten or hurt. You just called them in at dinner time. It was a grrreat place to grow up. The Nesbitts, the Bresnehans, the Wolffs, the Milburgs, the Tenkates, the Guthmans. What wonderful childhoods we had.

    • Love those memories! The Gaherins were fantastic neighbors. And you’re right — we did have wonderful childhoods. Thanks for taking me back there.

  41. Ruth Kaufman

    Hi Dan, Bob Selverstone sent me your wonderful memory of High Point Road…many thanks for reviving so many memories for Art and me and all 5 of our kids. It was a wonderful time of our lives. Best….Ruth Kaufman

  42. Hi Dan, What a wonderful reflection and sharing. Thank you so much. We lived and loved and laughed and cried on High Point Road. And we flourished to bring our love of life to many other parts of the world. I still visit High Point Road every time I pass through Westport, my pilgrimage to a place of growth and health and deep life lessons. Thanks for being our neighbor, and for being the wonderful writer that you are. Ron Kaufman