Three members of the Jennings Trail Committee, from left, Wendy Crowther, Morley Boyd and Peter Jennings, stand at the yet-to-be-disclosed site of one of the trail’s new markers. Not pictured are committee members Bob Weingarten and Robert Liftig. / Contributed photo by Bob Weingarten
Photo at left: The 23 points of interest on the Jennings Trail start with the first marker on Jesup Green. Mounted on small monuments, the plaques tell the story of Westport’s history on a tour covering nearly 20 miles. At right: George Washington visited at least two places in Westport, including the Marvin Tavern, which was located on what is now Post Road West. 

By Gretchen Webster

WESTPORT — From the Minute Man statue to the place where British soldiers crossed the Aspetuck River — and, yes, where George Washington had a meal — the Jennings Trail links 23 historic spots to step into Westport’s past. 

And soon there will be four more points of interest added to the trail, plus a digital guide to facilitate the tour.

The trail, first mapped in the 1970s, is dedicated to Bessie Cornelia Jennings, a teacher who conducted tours of historic Westport sites for her students and others. She was “Aunt Bessie” to Peter Jennings, although she was actually his cousin.

Photo at left: Peter Jennings, who has helped maintain the Jennings Trail of local historic sites for many years, is a descendant of one of the oldest families in Westport. At right: Bessie Cornelia Jennings, a teacher who loved history and led tours of local historic sites.

As he grew more interested in the Jennings family’s 10-generation legacy in Westport, Peter Jennings — joined by Morley Boyd, Wendy Crowther, Robert Liftig and Bob Weingarten — established the Jennings Trail Committee. The group, formed to maintain and expand the trail, was initially a project of the Westport Historical Society, now the Westport Museum for History and Culture, and the Westport Young Woman’s League.

Jennings and the committee have gathered donations and used their own resources to maintain and upgrade the trail for many years.

“They are an amazing group of historians,” Jennings said of the committee.

In 2018, Weingarten wrote the article, “Take a Hike,” about the Jennings Trail in the publication “Greens Farms Living,” now out of print. As well as including the story of Bessie Jennings and how the Jennings Trail began, Weingarten’s article also explains the historical significance of the trail and the value of understanding and learning from history:

The Minute Man statue on Compo Road South, one of the best-known of Westport’s historical symbols, is the ninth point on the Jennings Trail.

“Let us hope that those touring the Jennings Trail will not examine the sites as only landmarks, but will acquaint themselves with the happenings, experiences and opinions of those times,” Weingarten quoted Robert Gault, the Westport Historical Society president, as saying when the trail was under consideration.

Covering about 20 miles and winding over town roads, the trail’s points of interest are marked with small stone monuments topped with plaques explaining the site’s significance. 

The first trail monument is at the corner of Jesup Green near the Taylor parking lot. It’s the site where the Jesup family’s warehouses and wharves were located, “when shipping and farming were the basis of the economy,” according to the “Jennings Trail, A Guide-Map to Historic Westport, Connecticut.”

The last of the current 23 markers is at 46 King’s Highway South, the location of the Platt house, built as early as 1700, “possibly the oldest house still standing in Westport,” the guide says. Between the first and last monuments, people following the trail gain a wide-ranging overview of Westport history.

The location and significance of the four new markers to be added this year won’t be disclosed until they are installed, Jennings said. But the wording for the plaques has been approved, they have been ordered and as soon as there is official town approval for the markers’ locations, they will be installed, he said.

A 21st-Century addition to the trail — an online audio guide — was approved unanimously by the Historic District Commission on June 11. The online guide, produced by the company Otocast, is a customized audio tour that can be accessed by many devices, according to the company’s website and is already used by the Discover Westport website.

Photo at left: This Jennings Trail monument marks the location of a grist mill at Old Mill Beach, where boats loaded grain for the West Indies trade. At right: The boardwalk to the grist mill marker on the water’s edge is one of the more picturesque paths to a site on the Jennings Trail. / Photos by Gretchen Webster

The set-up cost of the digital tour is $3,375 to include all 27 points in the digital guide, according to Grayson Braun, chair of the Historic District Commission. The town’s annual cost to maintain the guide will be $1,350 going forward. The appropriation is coming from the HDC’s annual budget for 2024, she said.

Peter Jennings will write the script for the tour and offers to send anyone who wants a written guide to the trail before the online tour is ready. Email him at to request the written guide.

“The Jennings Trail is one of the few things left that keeps Westport history alive,” Jennings said. “We want to make it more accessible and raise awareness of the trail” and of Westport’s history.

Freelance writer Gretchen Webster, a Fairfield County journalist for many years, was editor of the Fairfield Minuteman and has taught journalism at New York and Southern Connecticut State universities.