Chester, Connecticut | Photographs
A collection of scenes from the picturesque village of Chester, Connecticut from photographer Caryn B. Davis.
Chester Point Marina with access to the Connecticut River.
Credit: Caryn B. DavisPhotographer Caryn B. Davis has been drawn to the Connecticut River Valley’s natural beauty ever since she saw it as a teenager on a road trip. After traveling around the world, she returned to Connecticut, camera still in hand, and began looking for a place to settle. Although she had never been to Chester, she landed there quite serendipitously when she decided to follow a road sign pointing to the town center. Following it, she found herself in one of the most picturesque villages she has ever seen. The year was 1999, and she has never left.
We asked Caryn to photograph the town of Chester, Connecticut as part of our ongoing “Could You Live Here” series. Highlighting towns with a small population, but plenty to offer in terms of a simpler way of life, the series celebrates the best of New England’s community spirit. Please enjoy this slideshow of some of our favorites from Chester, Connecticut.

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis

Credit: Caryn B. Davis








Beautiful photo layout and interesting review!
You’ve captured our little village beautifully, Caryn Davis! I especially love the bird’s eye view of the Chester-Hadlyme Ferry…Thank you for sharing your amazing work.
What a beautiful tribute to our former town.
Thanks to a recent acquaintance with a former, but faithful , resident of Chester who introduced me to your lovely state. I am very grateful to her and you too for having the pleasure of enjoying the lovely slides.
I hope one day to be able to visit and see it in nature. Thanks again. Jacob
I was just 17 years old, when I discovered the ferry boat ride across the river. 63 now, and how many trips across, or crusing through the back roads of Hadlym. East Haddam and Chester. After a day at Rocky Neck, I would drive up 9 and we all would go to the Chart House, with the water wheel and the great outside patio for margaritas. Those were the days…
My hometown! Rode my bike all over town as a child; from our house on Middlesex Avenue to Chester Elementary and even to John Winthrop Jr. High, downtown to Robbie’s and the Micceli’s pharmacy, fishing for brown trout below the falls at Jennings pond, to all my friends houses around town, and of course took my bike on the ferry (5 cents) to go visit and hang out at Gillette’s Castle. Lots of time down at the river at Parkers Point, pizza at Cozy Castle, and of course, the Chester Fair! Such a great town and wonderful place to grow up in the 60s – 70s!
Lots of small changes over the years, but still a fantastic, small shoreline town.
Just lovely to see my old stopping grounds and what a beautiful tribute. I lived down the road from the Chester ferry but on the Hadlyme side and my husband and I recently moved to Jackson Hole to retire. I’ll always be a New Englander and miss my old home.