Category Archives: Street Spotlight

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 dwoog@optonline.net. 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 dwoog@optonline.net)

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.