Friday Flashback #88

If you were a 2nd grader in Westport between 1959 and the early 1970s, you remember the Jennings Trail field trip.

Bessie Jennings (Courtesy of Greens Farms Living magazine)

Bessie Jennings — a native Westporter who traced her ancestry here to the 1650s — conceived, developed and led the tour after retiring as a history, government and civics teacher at Roger Ludlowe High School.

It included the Beachside Avenue site of the 5 founding Bankside Farmers; the Machamux boulder; the old Greens Farms Church meeting house; the Compo Cove tide mill; the Minute Man monument, and the Compo cannons, among many others.

She told stories about the Sherwood triplets, the tar rock signals sent when the British landed, and much more.

After Bessie Jennings died in 1972, the Westport Young Women’s Woman’s League worked with the Westport Historical Society to create 23 markers, at historic sites throughout town.

Of course, it was called the Jennings Trail.

One of the plaques on the Jennings Trail marks the Elmstead Lane home where Bessie Jennings was born, and died. (Photo courtesy of Greens Farms Living magazine)

(Hat tip to Bob Weingarten, Westport Historical Society house historian, who published a longer version of this information in Greens Farms Living magazine.)

9 responses to “Friday Flashback #88

  1. I’m a local graphic designer with a degree in architecture and interest in historical preservation. When I lived in the West Village of Manhattan I researched, wrote, designed and distributed a historical walking tour guidebook called “Remember NYC: The Meatpacking District”. It was distributed in all ground level stores, restaurants and galleries in the Meatpacking. I eventually sold the guidebook rights to the Meatpacking Improvement Association. Since the research and walking tour has already been written please contact me if you’re interested in creating a printed/distributed guide booklet of Westport. I’d be happy to work with someone on this!

  2. Michael Pettee (Saint Paul)

    I remember the field trip well with Mrs Torno’s 2nd grade class. The trip also included a tour in a colonial century house house with a huge fireplace in the dining room and they stood a number of us 2nd graders inside it should-to-shoulder, the well where the Brubaker(?) silver was hidden, and what we were told was the remnants of a colonial era onion barge in the Eastern side of the mud flat near the Saugatuck bridge.

    • The barge is still there, Michael!

      • It’s a ship. I seem to recall she originally hailed from New Jersey before being purchased by a Westport family for use as a market boat – I kinda think it was the Nash’s but could have it wrong. Pretty sure the ship’s name is/was the Adam Remson.

  3. Joyce Barnhart

    The Westport Young Women’s League led Jennings Trail Tours in the 70’s for second graders and, later, for third graders, I think. It included a stop at the Adams Academy and lunch at Compo. I learned that Compo is from an Indian word, “compaug”, that means “bears’ fishing ground” When I was a docent Connecticut history was studied in second grade, I think, and the tours were part of those lessons. It was tricky pointing out different sites as we rode around town because the bus engine was loud and we could talk only when the bus was stopped . I had fun taking my son and a buddy on the same tour when they were working on a history badge for Cub Scouts in third or fourth grade. There was also a tour for adults, maybe sponsored by realtors, that was recorded by Joanne Woodward and possibly Paul Newman.

  4. Bob Weingarten

    For those that want to read the full article you can find it on the Westport Historical Society website at The article is named “Take A Hike”. There are many other historical articles that can be found in this section of the WHS website related to Green’s Farms but have included historical information on the entire Westport.

  5. Jo Ann Davidson

    I enjoyed the Jennings Trail bus field trip with my kids’ 2nd grade classes, took notes on Miss Jennings’ stories, still have them…..somewhere.