Jennings Trail

The Westport Historical Society proudly presents the annual Jennings Trails program to all third grade students in the Westport schools each May.

This tour gives students a chance to learn about Westport's early history (1700's through early 1900's) by visiting two historic sites: Old Adams Academy (the original one-room school house) located on North Morningside Drive in Westport and the Bradley-Wheeler Barn, located at 25 Avery Place, Westport.

This is an interpretive tour with parents serving as guides at the sites and hands-on opportunities for the students to experience what life was like for people during the Victorian period. The Jennings Trail tour is dedicated to the memory of Bessie Cornelia Jennings, who was so enthusiastic about the history of our area that she conducted tours for second grade students in Westport schools throughout Greens Farms and Westport to give them an understanding of their town.

In addition, The Westport Historical Society offers a booklet called Jennings Trail: A Guide-Map to Historic Westport, Connecticut, that provides a history of Westport, and outlines a driving tour of two dozen plaques that mark historical sites in Westport. This booklet is available at the WHS for $1.75. Please call the WHS at 222-1424 or stop by at 25 Avery Place to obtain a booklet or for more information.

Local third grade students learn about kitchen history in the Victorian kitchen of Wheeler House at the Westport Historical Society. The cast-iron cook stove, dated 1870, was the most important item in the kitchen. Items such as the apple parer, pancake maker, coffee bean roaster, coffee grinder and lemon squeezer were guaranteed to shorten time spent in the kitchen.

Adams Academy

Nestled in a lovely grove of trees lies one of Westport’s unique treasures— Adams Academy. This one-room seat of learning, a preparatory or high school, was founded in 1837 by Ebenezer Adams and operated until 1867. 

The accomplishments of Ebenezer Adams still reverberate throughout our community today. A local resident, this remarkable young man returned to Westport after graduating from Yale to purchase and privately run an existing school on “Academy Green.” The school had been started by Reverend Davies of the Greens Farms Congregational Church. Ebenezer married the Reverend’s daughter and built their home on the corner of North Avenue and Long Lots Road (later made famous by Martha Stewart).

Children were publicly educated only to the fourth grade level, after which parents had to pay for private schooling. Well known as a teacher with high standards of excellence, Mr. Adams attracted students from all over Connecticut and states beyond. One local student, E.T. Bedford, became a wealthy financier, founded the Karo Sugar Company and was also a great philanthropist giving us the Westport Library, the YMCA and funds for public schools. Another student, William Marcey, became the Secretary of State under President Franklin Pierce.

Mr. Adams had an encyclopedic mind, single-handedly teaching many varied subjects including languages, sciences, mathematics and navigation (during the age of sea captains) to students of different ages and levels— all in one classroom. In the 30 years of the Academy’s operation, his 637 students were all admitted to universities, many to Yale.

This small beacon of enlightenment, which once served as the headquarters of the Historical Society, is now owned by the Town of Westport. The classroom museum is open for the Jennings Trail school tours in the spring and is also rented out to various organizations to help pay for its upkeep.