Post roads were some of the first roads established in New England and were used mostly by mail stages and post riders.
Following the Post roads, "turnpikes" were established by private individuals and corporations.
The name "turnpike" comes from the gate on a road to obstruct passengers. Today many of our major highways follow the old turnpikes, Route 103 being an excellent example.
The Green Mountain Turnpike was chartered by the Vermont legislature on November 3, 1799 and ran from Clarendon to Bellows Falls.
Among its first owners and incorporators was John Atkinson, the Englishman who also heavily invested in the Bellows Falls Canal and for whom Atkinson Street in Bellows Falls was named.
There were to be four gates on the road, one near its east end in Rockingham, one in Cavendish, one in Ludlow and one in Shrewsbury.
The 1816 "Journals of the General Assembly" in Montpelier shows legislature to establish a gate in Chester, but the act failed to pass. The tolls established by law varied from 30 cents for a single horse carriage or coach, to 56 cents if drawn by two horses. The rates were collected at each of the four gates.
If any person should turn out for the purpose of going around any gate, he should forfeit triple toll as a fine and plain signs should be displayed at each gate showing the rates of toll.
"Shunpikes" were roads that skirted around turnpikes, where no tolls had to be paid, thereby shunning the turnpikes. Today you will still see some roads in Vermont marked as a shunpike.
A charter was granted in 1807 to a company for the building of a turnpike, connecting with the Green Mountain Turnpike at Chester and continuing over the mountain to Manchester.
This later became a part of the most popular stage route between Boston and Saratoga Springs.
The intersection of these two crossroads in Chester made for a major hub of activity. All commerce and individuals travelling from Montreal to Boston or Albany to to Concord, NH, had to come right through town.
Numerous inns and taverns were built in Chester to accomodate all of the travellers. Two of these inns remain today, the Henry Farm Inn and Kelly's Tavern.
Chester was a wealthy and prosperous town inhabited by highly educated men and women, and became a highly sophisticated and modern town both in its residents and architecture. It was also said that Chester had some of the best roads in the entire state.
These turnpikes were built and maintained by private capital for about 40 years, after which the different towns through which they were laid, purchased them to become important parts of the present highway system of the state.
Sources used for this article included: The Connecticut River Valley in Southern Vt and NH: Historical Sketches, 1929, 1816-1827 State of Vermont Journals of the General Assembly.