Tag Archives: High Point Road

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.)