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COVID + 5 Years: Westporters Look Back

Dan Woog

Five years ago this week, Westport was just settling into the new reality of COVID.

The weekend’s nice weather had brought large crowds to Compo Beach, though the parking lots were closed. Town officials — worried about close contact (even outdoors), and cars parked all along Soundview Drive — scrambled to react.

Soundview Drive, the first weekend after the lockdown. Town officials quickly cracked down on parking there.

The Trader Joe’s line wrapped along Compo Acres Shopping Center storefronts. Only a few shoppers were allowed in at a time. The checkout line was — like every other part of life — dictated by “social distancing.”

Schools desperately tried to figure out “distance learning.”

Trader Joe’s enforced social distancing rules — with their own very recognizable font.

And that was just the first couple of weeks.

Five years later, how have we changed? What effects linger — negative or perhaps positive? What do you remember most about those uncertain, frightening days?

Earlier this month, “06880” asked readers to weigh in. Here’s what you said.

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At the beginning of the pandemic, I was living with my husband in a very. comfortable house. He had a heart condition, but we enjoyed what we had, and managed to do many things. Then COVID struck, and I learned that my best friend from high school was one of the first 1000 deaths.

In May we decided to move to a senior housing domicile. It was beautiful, and well-maintained. My beloved husband lived there for 5 days; then he passed (from his heart condition). A few weeks later, I was diagnosed with COVID and quarantined for 15 days in a new home, where I knew no one and was totally isolated.

So I can’t say that the pandemic treated me favorably. I’ve gotten all the shots I could possibly need to protect me against the next outbreak of something — I hope. — Bobbie Herman

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We were raising our son in a 1- bedroom apartment in Greenwich Village. Wanting more space and family, we gathered a few things and our cat, and went to stay with my mother in my hometown of Westport. We expected to be there a few weeks, a month at most.

As spring and summer passed, my husband and I got used to the spaces, the beach, the green. We got spoiled with multiple bathrooms, a convenient washing machine and drive-thru Starbucks. We got to know the town better, the stores, the people, and eventually looked into the schools. When we saw that a cute house was less than a decent 2-bedroom in our neighborhood (crazy, this was 2020) we decided to stay.

Five years later I miss New York terribly. I miss my community, and easy access to all that culture. But I am happy with our decision to stay. We have settled nicely, embraced the town that has changed so much since my childhood yet is so familiar. I knew we were settled in when we did something I would not do in the city: adopted our dog. —  Juliet Koskoff Diamond

Late March, 2020: Starbucks’ drive-through was one of the few places that seemed normal. So long as you didn’t get out of your car. (Photo/Rob Hauck)

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Not for all, but it was a glorious time for my husband and I. We started the pandemic as new grandparents. Our daughter and her husband moved from the city into our home, thinking it was only temporary.They ended up purchasing a home in Fairfield. Now we have 5 grandchildren, 4 of whom were born during the pandemic (the first was 5 months before. That’s how our life changed, all for the better: It gave us an immersion of love and family time.

And we never got COVID — until last July. — Dorothy Robertshaw

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I was a “COVID person.” My husband, our son (who was 3) and I moved to Westport right before official lockdown. We didn’t know a thing about the town, only what our realtor told us. We didn’t have much time to decide so moving here was definitely rushed.

Turns out, it was the best decision. A few years later after restrictions loosened we could really discover the town. COVID was the worst thing to happens to us in a very long time, but it led us to Westport and for that, we are thankful! — Cubie Vinson

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We experienced grand plans interrupted. Our daughter was studying abroad in Cannes, excited for the culmination with the Cannes Film Festival celebration (she’s a cinematographer), our son was a senior at boarding school and navigating college acceptance and revisit days. Some amazing trips booked for my hubby and I. All of which cut short with kids returning home — the lovely silver lining to the COVID cloud.

 

I personally managed group purchasing contracts with hospital systems across the country. We manufactured systems/kits for infectious disease testing at hospitals, VAs, clinics. I was part of the pandemic response trying to allocate kits. We were not prepared to manufacture at a rate beyond understanding. It was insane. And just when we thought it was subsiding, the surges would hit again, and again.

Five years later: Kids graduated, happy and working. Squeezed in a few trips with my hubby. Me? I left the COVID-induced crazy corporate life, having gratefully served the pandemic response that culminated a career in diagnostics, to open a chocolate shop — in Connecticut of course! Life is sweet with a little bite of happy. — Laureen Haymes

Remember COVID testing? This was the scene at St. Vincent’s Medical Center on Long Lots Road, a few days before Christmas 2020. (Photo/Randy Ford)

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In April, during the beginning, my wife and I were blessed with our first grandchild. We had to visit while standing outside the sliding glass doors of their home. We had our second grandchild 2 years later, but we still had to do all of the precautionary steps. We then had to visit my wife’s aging parents at the nursing home while standing outside of their window (thankfully they were on the first floor).
When we opened back up at work (framing shop), we went from gallery exhibits to appointment only, which the clients actually liked, so we kept that for a while. Now I take appointments if the client prefers but it is “walk-ins welcome” again. I keep masks on hand and sanitizer if that makes a client feel more comfortable. How did it change me? After the two shots and one booster, I have a constant white noise. — Jay Cimbak
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We really never changed our lives. We entertained, got together with friends, traveled again to Croatia and several other international destinations .., easy to use points. No crazy panic as in the US, life continued, kids went to school and learned. It was just another illness like measles and diphtheria — except this escaped from a Chinese lab and globally spread because of global travel. — Jeff Schaefer
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Real estate market prices of home values have skyrocketed. Long after COVID was over, Westport was exponentially higher than other neighboring towns to move to. More commercial spaces are occupied as well, lot of growth in town plus the population increase.
Lot of new residents, excited to live here and find that “home” feeling but also get used to the constraints of living in a town that was first settled in the 1600s by the Bankside Farmers. Fridays in town during “rush” hour is a reminder of the relaxed COVID days, but before that, going from Westport to Greenwich or the NY border in under 30 minutes was heaven. No traffic.

Towns have their ups and downs. Can we continue to keep climbing, or will the demand soften and relax and slow development, enrollment rate and demand to live here? — Andrew Colabella

Commuting patterns changed dramatically durng COVID. This was the Westport trian station in May 2020. (Photo/Caroly Van Duyn)

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The permanent change is to mental health, and I’m not sure it recovers. If you Google “US School Shootings,” post say 2022 is pretty horrific. 115 and 116 in 2018/19/20, 327 in the school year ending 2023. Isolating kids, not great, although many Fairfield county towns did a nice job opening fall 2020 classrooms.
Adults haven’t fared much better. Employers have had to threaten and/or beg their employees to come back. Many of us have big jobs with big responsibilities and big benefits so we comply, but large swaths of America are still entrenched at home even in 2025. Good for some, bad for most.

It’s easy to second guess all the decisions, and there were bi-partisan wins and losses. I remember on 9/11/01 thinking that was the most traumatic thing I’d go through. In some respects, the lingering effects of the pandemic have been way worse. — David J. Loffredo

(Since 2009, “06880” has been “where Westport meets the world.” If you enjoy this hyper-local blog, please click here to support our work. Thank you!)
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