By Lisa Cummings
I remember one of my first visits to Westport, when I lived in New York City back in 2008. My husband and I had friends here. We would get invited to their parties. We weren’t parents yet. Our friends had kids at Bedford Middle School. Everyone seemed to be living their best lives. Easy access to the city, right on the ocean, excellent public schools, some tennis, golf, grilling by the pool, great restaurants. I said, “I think the people in the suburbs have more fun.” It’s true. My husband and I moved to Westport two years later in 2010.
The house we live in now is the first house we looked at. We bought a traditional farmhouse-style home in beautiful Greens Farms that had just been gut-renovated. We fell in love with it and moved here in September of that year. Eden, our daughter, was born a month and a half later.
It’s been 15 years now and not one regret. It’s where we started our family, got our first dog and made some core memories. I’m from the Boston area and spent my summers on Cape Cod, so Westport felt very similar. It was easy to make connections because this community offered so much.
You can dial it up or down here. That’s what I love about Westport. One week I could be at a fundraiser or fashion show at The Westport Library, and the next week I could be meeting a girlfriend at the Farmer’s Market or having a casual family lunch at The Sherwood Diner (I never get sick of the kale salad with salmon or chicken). The shopping downtown has gotten more elevated, which I love. Some of the brands, like Unsubscribed and Vuori, are great, but I also love popping into Roundabout for designer consignment.
We love supporting Bedford Acting Group and Staples Players since my now-teenaged daughter has a huge passion for theater, singing and the arts. How lucky are we to have access to all of this?
On a given day, if I’m not working in my art studio on an illustration job, you might find me at the Double L Market for the best fish, meat and produce to grill that night. Lloyd and his wife Gianna feel like family. I might hit a Pure Barre class, which has been a consistent highlight of mine throughout the years, but I also love my Compo Beach walks and weekly tennis clinics at Sylan Tennis Club.
Truthfully, what I love most about Westport is sitting out by our pool with our dogs, all the hydrangeas in full bloom, reading, and watching our daughter hang out and swim with her friends. It feels like a full-circle moment.
Watercolors by Lisa Cummings