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 email@example.com. 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.
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).
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.
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.
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.
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 firstname.lastname@example.org)