From Dorchester to Windsor: The Founding Trek and its Recreation

Last weekend, Connecticut celebrated a statewide “Trails Day” in an effort to get people outside and exercising. Trails Day was a weekend-long event encouraging people to see a little bit of the world that existed before civilization. In the spirit of Trails Day, this week we take a look at one of Windsor's most recent memorial treks, and the monumental hike that inspired it.

In 1983, Windsor was celebrating its 350th anniversary. During the early months of the year, a massive celebration was being planned to commemorate the founding of Windsor, Connecticut's first town. Donna Siemiatkoski, the chairwoman of the Windsor Founder's Observance committee, felt that it would be appropriate to plan a trek that followed the original settler's route as closely as possible.

It was in 1633 that a trading post was established on the ground that is now present-day Windsor. Nothing more than a small bastion in the woods, Windsor's very first settlers were nothing more than merchants with a small force of arms. They came to the central valley by sailing a trading vessel up the Connecticut River.

To the north, in 1635, a group of Puritans landed in Dorchester, Massachusetts. These settlers sought an area to establish a new settlement. The plentiful farming soil of the Connecticut Valley beckoned. During that summer, the Reverend John Warham led a group of nearly a hundred people over 100 miles. They followed a Native American route to the area once referred to as Matianuck. We now know it as Windsor.

This is the journey that Siemiatkoski sought to recreate. Laurel Ledgard described the trek in a Boston Globe article titled “113 Miles of History – a foot at a time”. In it she asked Siemiatkoski about her reasons for undertaking such an extraordinary task. Her response highlighted a desire not just to know, but to experience her ancestors' trials.

“My ancestors made the original walk and I wanted to do it,” Donna said at the time of the walk, “I want to feel what they felt and experience some of the hopes and fears they had.”

Windsor's original settlers referred to their route as the “Old Connecticut Path,” a name that implies that it existed long before Europeans began colonizing the New World. Siemiatkoski's group would follow this same path as close as possible. The entire route was estimated at 113 miles. About 3 dozen Windsor citizens would be recreating the journey together.

The 1983 group, sponsored by the Descendents of the Founders of Ancient Windsor, began their journey at Savin Hill Beach in Dorchester, MA. They had successfully planned to finish on Windsor's Palisado Green some ten days later. A large truck would carry gear, wary travelers and provided medical assistance. A pair of nurses also traveled with the group. Also, the group had rules that they would abide by en route. They were allowed gas stoves, but were not allowed any ice on the journey. Fast food was strictly off limits.

As the AP reported in the article “Hikers follow route taken 350 years ago,” the group would stay in churchyards and campgrounds along the way. Their first night was spent at the Dorchester Congregational Church. Upon their arrival, the Reverend James K. Allen blessed their journey and “welcomed you [the group] here, where you begin again to walk through history. We wish you Godspeed on your way.”

The group consisted of several Windsor residents, including Tony Greco, nearly the entire Siemiatkoski family, and several members of Windsor's boy scout troops. But the most peculiar traveler was certainly Kent Avery. Kent walked the entire 113 miles barefoot. Bob Vacon, a writer for the Journal Inquirer, reported in the August 26 article “Re-Creation of Windsor trek almost over for 30” that the young man had always preferred to be shoeless.

A whimsical Avery stated that “Since I was little, I never liked to wear shoes, so whenever I can, I go barefoot. I don't have any blisters, and the only problem is a little tar stuck on my toes from walking on a road they had recently tarred.”

Nevertheless, nearly the entire group finished the journey. On September 1, 1983, these modern day adventurers finished their hike to Palisado Green, including the barefoot journeyman, right on schedule.

This article was written utilizing resources provided by The Windsor Historical Society. The Windsor Historical Society staff was not involved in the fact checking process of this article. Any opinions within this column do not reflect the viewpoints of The Windsor Historical Society or its staff. You can visit the Windsor Historical Society at www.WindsorHistoricalSocety.org.