Sketching Roots

Elaine Clayton is a longtime Westport. She’s been an “06880” reader from the start, 11 years ago. She’s an artist too, with a passion for sketching her home town.

But despite her many years here, Elaine had no idea how strong her roots are. She writes:

Lately my sister has been exploring our family tree on my maternal side.

She asked if I realized we had ancestors in Westport. I did not.

It turns out my 8th great-grandmother was Abigail Sherwood (whose nephew Daniel was the original owner of Sherwood Island).

Sherwood Island (Elaine Clayton)

In the same family line — which includes Ogdens and Jenningses — my g-grandfather was Joshua Jennings I,; my great-etc. uncles were Joshua Jennings II and III. They married into the Sturges, Bulkley and Burr families. Ogden House on Bronson Road in Fairfield was a many times great uncle’s house.

I had fun too contacting a new-found cousin, Peter Jennings.

This fascinates me, because I have gone around drawing as much of Westport and Southport as I could. My younger son is part of the town too, tending to the beaches and fields with the town crew.

Compo Beach, from Soundview (Elaine Clayton)

How far do your roots go back in Westport? Check them out. They may be deeper than you think! Let us know your links — click “Comments” below.

15 responses to “Sketching Roots

  1. James Honeycutt

    My earliest roots with Westport only go back to the days in the early 1970’s when the band Repairs that I was in at the time performed each week at La Crepe and Mark’s Place in Westport. After leaving the music business around 1975 or so I tried my hand in teaching based on the recommendation of a college friend and Westport teacher Richard Heggie. I subbed for two years in Westport, got a taste of education in Westport and returned in the fall of 1977 to begin to teach at Coleytown Junior High School along with Richard Heggie, who himself taught there. After a few years, I transferred to Long Lots Junior High School and taught next door to a young Spanish teacher Denise Barberio with whom I became friends and eventually married. We both retired in 2016 from Westport Schools having both had a wonderful career and experience in this Town. While my roots do not go as far back as some Westport, both Denise and I love the Town.

  2. Elaine, we’re seemingly related in some manner as Peter Jennings and I are related too (our Westport Jennings line descends from Joshua, b.1620, as well). With regard to the Sherwood family and connections we might possibly share there, my 5th great grandfather, David Sherwood, married Abby Meeker; their daughter, Elizabeth Sherwood, married Gideon Jennings. I have nice little portrait of Elizabeth’s sister, Deborah (b. 1813, m. Walter Jennings) that a friend gave me.

  3. Like Jim Honeycutt, I am a relative newcomer (since my family only moved here in 1963).

    My brother and I, though, possibly hold a unique place in Westport history. Our family moved here in the spring, and our first day in Westport schools was April Fools’ Day. I tend to doubt any other kids ever had their first day of classes on April 1. And I am happy to report that no one played any pranks on me that day!

    I also remember that two of our earliest meals here while we were house hunting (and possibly that first weekend) were at Westport landmarks: Big Top and the Ice Cream Parlor.

  4. Good work, nice story
    Do you want to be interim selectman while ours is isolating!!

  5. Jarret Liotta

    Lovely paintings, Elaine!!

  6. Elaine, I loved reading about your history. It reminded me of a real estate agent with whom I worked by the name of Alice Jennings Benson. I bet if you did a bit, you might be related to her as well.

  7. Welcome cousin Elaine. I too am related to the Jennings, and Sherwoods, and Burr, and well, all of them. Through my mother’s family, the Mills family, I can trace my roots back to at least three of the original Bankside Farmers, so I guess my Westport roots run pretty deep.

  8. I am so grateful to all these wonderful comments. I’m so excited to connect with cousins! This is really enriching. I’d love to get everyone’s email–one way would be to send me a message through my website (safer than putting an email here). The fact that my younger son has been working with the town crew (took a gap year and then the pandemic happened) and taking care of the fields and beaches that once were his g-grandparents (this also includes a Sturges g-grandmother) it really is mystical to me.

    Ilene Goby, I’d love to share Jewish ancestry with you, can you email me or message me on FB?

    Fred Cantor, April Fool’s Day and Big Top and the Ice Cream Parlor all sound like a big happy good luck welcome!

    Lynn Flint, I’d be terrible at it!!!

    James Honeycutt, I loved reading your recollections and just having the things about the town that we all have enjoyed, I moved here in 2007 and so the friends I have (and now newly found cousins) mean a lot to me.

    Jared, I had so much fun working w/ you via the library and following your new film work!

  9. Pete Jennings is a longtime friend and the official historian of Greens’ Farms Church

  10. Peter Jennings Talbot

    Hello cousin Elaine! I too go back to all the Joshua Jennings, and have many Burrs, Sherwoods, Bulkeleys, Morehouses, etc in my line, coming down through the aforementioned Joshuas, David, Jesse, Gideon, Austin, Erwin and my grandfather John Morehouse Jennings. We have a king and distinguished line and branches encompassing the history of Greens Farms, Westport, and Fairfield County.

    – Peter Jennings Talbot

  11. There was a beloved custodian at Greens Farms School known as “Pop” Jennings. He had a heart attack in 1956 and was told he shouldn’t climb stairs (would they still give that advice today?). Fortunately Burr Farms School was to open all layed out on one level, so he transferred there. Unfortunately a second heart attack soon killed him.

    He had a daughter Grace who was the ticket agent at Green Farms Station (as the railroad called it), and protests were made when the railroad decided to close the ticket office with an agent only on Mondays.

  12. Enjoyed the comments especially those where new family connections have been made through ancestral relations. My brother is quite the genealogist and found that we are directly connected to the Gorhams, early West Farms settlers. Here, for your reading pleasure (or not) is the connection which include a good number of familiar original settler family names…
    6G Grandfather Joseph Gorham (1692-1773)
    Born 22 August 1692 in Bristol, Rhode Island, and settled in (Greens Farms) Westport, CT, about 1715. He married 6G Grandmother Abigail Lockwood in 1715 in the Greens Farms Congregational Church. Abigail died in 1725 and Joseph married second 6G Grandmother Deborah Barlow, whose mother was 7G Grandmother Ruth Sherwood. Her father was 7G Grandfather Daniel Lockwood. Joseph fathered an impressive 12 children, six with Abigail and six with Deborah. Abigail and Joseph’s children include Ichabod, our 5G
    Grandfather 1724-1799. We of course know about the presence of the Gorham name around town (road, island, etc) but had no idea that much of our DNA is located in (or more properly within) the old Greens Farms cemetery. One could even say we found our original family tree as ol’ Joe is now very much part of an aging oak (see photo if it managed to be attached). 5G grandpa Jabez is close by. Fortunately, his immediate family thought to provide a slate headstone which, unlike poor Joe’s, has survived the ravages of air pollution from route 95. MY brother insists there are still other “branches” to find! As I think on it, I find that it is both an odd yet somehow comforting feeling to know that members of ones’s family going back 6 generations are still present only 1 mile from home.


  13. Elaine Clayton

    I so appreciate these thoughtful comments and I look forward to some kind of Cousin Get Together, maybe around Sherwood Island? In spring or summer. Please send me a message if you want to connect before that through my website!

    Reading all these has made me feel connected to the past with all the memories and with some joy in new experiences to come.

  14. Elaine Clayton

    PS I more than “like” all these wonderful comments, I LOVE them–I was not able to click on the “Like” bec a weird window opens up (?!!) and insists I need an account to do that. Have not figured out why!