8 Miles Away: That time I had a pen pal who lived in Westport, Connecticut

Tim Hammill
40 Days to 40
Published in
4 min readOct 13, 2020

While writing yesterday’s post, My Love Letter to Bridgeport, Connecticut, I was reminded of a story from my childhood that gave me a better understanding of the world outside of my hometown. I almost included it in yesterday’s post, but I changed my mind and decided to give its own post. So, here it is…

My class in fourth grade participated in a pen pal program. For the young people who may have accidentally stumbled up on this, pen pals are strangers who communicate via an exchange of hand-written letters delivered by non-electronic mail, better known as the U.S. Postal Service.

Why write a hand-written letter, which is usually just sentence after sentence about your pet fish and little league and how vegetables are gross, to a stranger? Good question. I don’t know. Here’s what my good friend Wikipedia says is the point of this pen pal thing,

A pen pal relationship is often used to practice reading and writing in a foreign language, to improve literacy, to learn more about other countries and life-styles, and to make friendships.

Typically, pen pals are a very long way of away from each other. They’re often times worlds away. The pen pals me and my fellow fourth graders at St. Augustine School in Bridgeport were paired with were also a world away, in Westport, Connecticut.

The distance between the two schools was eight miles. But it might as well have been 8,000.

Prior to our pen pal program, the nine-year-old me had never heard of Westport, despite it being just two towns away. I didn’t know anyone from Westport and didn’t really have a reason for going there. This was long before they had a Shake Shack, which ranks number one on my list of reasons to currently go to Westport.

I honestly do not remember anything about those letters, only that it was something that happened. For me to not have a single memory about those letters is probably a sign that they were just ramblings about the super unexciting lives of nine-year-old boys in Connecticut. But what I do remember very vividly from this little initiative was the day we went to go meet our pen pals.

My school, St. Augustine (now known as the Catholic Academy of Bridgeport) is located in The Hollow neighborhood of Bridgeport. The Hollow is the most densely populated neighborhood in the most densely populated city in Connecticut. The Hollow is also home to several immigrant communities, with approximately 30 percent of its residents being foreign born.

And so, my fourth grade classmates and I get on a bus and ride from The Hollow neighborhood of Bridgeport to Long Lots Elementary School in Westport — an eight mile drive down I-95 South into what we call “The Gold Coast.” That’s the name given to the affluent towns along the coast of the Long Island Sound starting in the west in Greenwich near the New York border and ending in the east in Fairfield, which is the town right next door to Bridgeport. In case you’re wondering, Bridgeport is NOT a part of The Gold Coast.

I’m sure there were good intentions behind creating this pen pal program, bringing together kids from very different backgrounds, yet oh so close to each other (seriously, Bridgeport to Westport is about one Freebird away). But, all this pen pal thing really did was show me just how well off our counterparts in Westport were.

That became clear to me before our bus even pulled into the parking lot of their school. And even more clear when our trip to their school started in their posh auditorium, complete with the kinds of seats they had in the movie theaters. This was quite the contrast to our school’s auditorium, which was furnished with the kind of folding chairs Mick Foley made a fortune getting hit over the head with. Our auditorium was also used for gym class, which was usually only half-court basketball games.

We shadowed our pen pals as they went on with a typical day of school. What was just a plain old Tuesday or whatever day to them, felt like we were taking classes in an amusement park inside of a museum with a cool gift shop. This was nothing, I mean nothing like a day at St. Augustine’s.

Was the point of all of this to open our eyes to what we didn’t have? If so, mission accomplished. If it weren’t for our pen pals, I wouldn’t have figured out the disparities between us and them until I was a little bit older. This naïve nine-year-old just assumed that schools were pretty much the same. Man, he was wrong.

I think I would’ve preferred to just keep writing and receiving hand-written letters about Garbage Pail Kids or Nintendo games over meeting our pen pals in person. I’m sure this experience for the Westport kids gave them some sort of educational enrichment, but all I got was seeing what being rich meant.

Tim Hammill is a communications professional in the nonprofit sector. He’s turning 40 on October 20, 2020. He’s writing about the final stretch to this milestone age in 40 Days to 40, a collection of stories, thoughts, reflections and whatever else comes to mind each day. In addition to writing a blog, Tim has also decided to donate his birthday to This Is My Brave, an organization he very recently learned about that brings stories of mental illness and addiction out of the shadows and into the spotlight. If you’d like to support Tim’s birthday fundraiser, go here.

Additionally, there are three other organizations that are close to Tim’s heart: Save the Children, Stand Up To Cancer and the Bridgeport YMCA. Click on each to learn more and to support their work.

--

--