From The Connecticut River Valley in Southern Vermont and New Hampshire: Historical Sketches by Lyman S. Hayes, Tuttle Co., Marble City Press, Rutland, VT., 1929, page 72:
COURT HOUSE AND JAIL AT CHESTER FOR CUMBERLAND COUNTY
In the neighboring village of Chester, in the section known as "Factoryville," stands a small stone marker near the residence of F. P. Burbank which indicates the location of the first court house and jail erected in what in later years became the State of Vermont. The circumstances of its being built, and its use, form a most interesting story of the primitive conditions surroundding the lives of the earliest settlers in this region. The spot was not marked until 1909, but the location of the building has always been a matter of record.
Previous to 1765 the few straggling settlers that had come to this section of New England had been obliged to go to .Albany, N. Y., about 150 miles distant, for all court matters, which with the lack of roads was a serious matter. Early in that year a petition was made to Governor Colden of New York for the establishment of counties in the territory between the provinces of New York and New Hampshire. In 1766 the Provincial Legislature of New York erected a connty comprising nearly the same territory now contained in the counties of Windham and Orange. They named it Cumberland County, and it was the first county to be formed in the territory which afterward became the State of Vermont. It was probably named for Prince William, the Duke of Cumberland, who in 1746 met with distinguished success in opposing the rebels in Scotland. The shire town of this new county was located at New Flamstead, the name later changed to Chester.
One of the principal reasons for the location of the shire at Chester was that Thomas Chandler, who was [73] a man of large means in those early days and resided there, made the offer that he would "at his own expense build a good and sufficient court house and jail." Four years later, in 1770, it was described as being in the corrner of a dwelling house built of small poles notched toogether at the corners similar to log houses. The corner considered as the jail was built as a palisade with upright poles six inches in diameter resting on the lower floor and reaching to .the chamber floor, pegged up with wooden pegs. The whole side could be easily thrown over and the prisoners freed. In this early jail at Chester there is record of but one prisoner being confined for any length of time, and he stayed there of his own volition because the man who had brought suit against him, and thus caused his confinement, "had used him with great tenderness and should not be made blameable for his escape."
In 1770 the inhabitants of Chester raised money by subscription, the unique document reading as follows: "June 16th-To Encourage the finishing of the Gaol now begun in Chester, we the subscribers will pay to such person or persons as Thomas Chandler, Thomas Chandler, Jr., Esquires, and Mr. John Grout, who shall employ labor or provide materials, the sums against our names written,-witness our hands,–Joseph Wood, one bushel of corn. William Dean two Bushels of wheat delivered at Rockingham at the last day of August." Judge Chandler then began the erection of a second building to be used for both court house and jail. The next year he complained that no one had paid in anything on his subscription, but he had built the second jail. This second jail was built of hemlock logs 20 inches [74] in diameter. Owing to the scarcity of nails, which were not manufactured by the colonies, the roof could not be completed and the new jail was left unfinished. In the meantime the old jail had been accepted by the court although it was questioned whether it would hold a prisoner who really wanted to get his liberty. Judge Chandler had the old jail repaired, the sides strengthhened, and, at right angles with the logs which formed the main body of the house, other logs were pinned.
Early in 1771 the inhabitants of Cumberland county, especially those on the Connecticut river, began a strong movement to get the shire removed to Westminster as being a locality more accessible. To prevent this Judge Chandler proceeded to build a court house and jail at his own expense. It was "thirty feet long, sixteen feet wide and eleven feet posts." Besides the court room, there was recorded a "sufficient lobby, or room fit for a jury, with a fire place in it." This building was leased to the county by Judge Chandler for a period of ten years, and as much longer as the county might want it.
In spite of having the use of these "commodious" quarters the people continued the effort to get the shire removed to Westminster, and these efforts were successsful. Supervisors were elected in each town in the county, who met in Chester on May 26, 1772, and selected Westminster as the shire town, designating the exact location for the court house and jail, which were built and first occupied in 1773. Its cost was limited to two hundred and fifty pounds, raised by tax upon the whole county.
This Westminster court house and jail were destined to become the scenes of many of the important events which occurred during the Revolution and the formation of the State of Vermont.