First Selectwoman Jen Tooker’s Love Letter To Westport

Photography by Andrea Carson

I fell in love with Westport in 2008. We were moving back to the U.S. after several years in London and looking for a home in Fairfield County. There are many beautiful towns in the area that met our criteria, each with its own unique charm, and we were excited by the possibilities.

I remember the first time I rounded the corner at Ned Dimes Marina and drove through Compo Beach so clearly. My husband Mo and I were immediately taken with the beauty of the coastline, and by the end of the day we had seen enough of the town to know that this was where we wanted to raise our family.

Compo is still one of my favorite places, and I spend as much time there as possible, walking with Second Selectwoman Andrea Moore on Saturday mornings or just relaxing on the beach. The coastline is beautiful all year round, and there’s a wonderful feeling of community among the walkers, bikers and runners.

Stand up paddleboarding on the Saugatuck River is my favorite way to experience Westport from the water. There’s something incredibly peaceful about being on the water and experiencing the sights and sounds of the river while floating past lovely homes and vibrant businesses.

We live in an exceptionally beautiful town, but I quickly came to realize that Westport is so much more than that. Westport is home to the most engaged, thoughtful and caring community I’ve ever experienced. It’s our residents and business owners, our teachers and everyone who works and volunteers at our schools, the volunteers and donors who work tirelessly to support Westport’s cultural and nonprofit organizations, our first responders, and our town employees and staff that make Westport so special.

From the beginning, I wanted to be a part of this community. I began volunteering by coaching soccer at first. Quickly, I was drawn to local government and was appointed to the Conservation Commission, then went on to serve on the Board of Education, Board of Finance and as Second Selectwoman, meeting many wonderful people along the way.

My respect and admiration for the people of Westport grows stronger every day. I love that we prioritize our children through our excellent schools and an abundance of activities designed to enrich their lives. I love that we recognize the importance of our senior community with an amazing Senior Center which runs more than 40 programs weekly. I love that we care about the environment and preserving the natural beauty of our town. I love that we continue to be known as an arts community.

I love how the whole town comes out for the Memorial Day Parade and the Fourth of July Fireworks. I love our vibrant business community, arts and cultural organizations and nonprofits.

I love how we face every challenge together, with respect and support for one another. I love that we’re always striving to be a better and more welcoming community — a place where everyone feels like they belong.

These are just a few of the reasons that Westport is the best place to live, work, play and learn in the region. There is truly something for everyone here.

I hope to see you out and about in some of your favorite places, and I’d love to hear what you love about Westport!


Jen Tooker, Westport First Selectwoman

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