On the Road to Woodstock: The Royalton-Woodstock Turnpike
By Jennie Shurtleff
Like many Vermont towns, Woodstock started out in the late 1700s with just a sprinkling of settlers. However, by the 1830s, Woodstock was one of the largest towns in Vermont.
There are several key factors that influenced Woodstock’s early development and led to this incredible growth. First, Woodstock was fortunate to have within its boundaries several major streams that provided water power and encouraged early industry. Second, in 1786 Woodstock became the shire town, or county seat, for Windsor County, thereby making Woodstock a political destination. And third, at an early point in its history, Woodstock became the terminus of two roads, the Royalton-Woodstock Turnpike and the Windsor-Woodstock Turnpike. These roads made Woodstock more readily accessible and thereby encouraged greater settlement and growth.
The Royalton-Woodstock Turnpike, which is the subject of this article, was chartered in 1800, and the road was laid out and built by a private corporation called the Royalton and Woodstock Turnpike Company shortly thereafter. To offset the cost of their investment and to finance the continued maintenance of these roads, the Royalton and Woodstock Turnpike Company charged travelers a fee, called a toll, which was collected at various toll gates along the road.
The story of the Royalton-Woodstock Turnpike is a somewhat complex one. While there are several historic sources that discuss this road, some of the dates and information appear to vary from one source to another. However, overlooking these inconsistencies, the general storyline for this Turnpike appears to be as follows.
After completing construction of their turnpike, the Royalton and Woodstock Turnpike Company erected the turnpike’s southern-most toll gate about 3 ½ miles from Woodstock’s court house. Because the toll gate was located 3 ½ miles outside Woodstock Village, it meant that many living in the Woodstock, North Bridgewater, and South Barnard area were able to use the last few miles of the toll road without passing a tollgate, and therefore without having to pay a toll.
About 6-8 years after the Turnpike was completed, the Turnpike Company decided to move the tollgate closer to what is now Woodstock Village so that the tollgate was set up just south of where the North Bridgewater-Barnard Road intersected the Royalton-Woodstock Turnpike (some three rods or so from the bridge in Willow Vale Center – what is now part of the “Pomfret Road” in Woodstock).
Although the location of the gate had changed, and travelers on the North Bridgewater-Barnard Road had to now pass by the toll gate, most of the gate tenders, according to Henry Swan Dana’s History of Woodstock, did not “take toll of any person who lived in Pomfret or North Bridgewater that passed the gate, nor of any person living in Woodstock who was going to any part of Pomfret, or who went the Gulf road to Barnard, unless they went north of Barnard meeting-house… and all persons living in Woodstock, north of the gate, passed the same toll-free.” There were also a number of others who were exempted from paying tolls per the Royalton and Woodstock Turnpike Company’s charter. These exemptions included those who were going to meeting, to the mill, on military duty, as well as those attending to “family concerns.”
Given the latitude in these guidelines for charging tolls, it appears that at least most of the local people were not charged heavily for using the road and that the relationship between the local people and the Turnpike Company was generally an amiable one until the year 1838, when David Bosworth became the Turnpike’s proprietor.
Village Square. Intersection of Elm and Central Streets.
This photo showing the intersection of Elm and Central Streets (which were previously the Royalton-Woodstock Turnpike and the Windsor-Woodstock Turnpike). The early presence of the turnpikes made Woodstock more accessible and brought travelers to the town. © Woodstock History Center
Roads before the shunpike
This detail from an 1832 map of Woodstock has been adapted to show the road from North Bridgewater and Barnard (in green) and the southern most part of the old Royalton and Woodstock Turnpike (in blue). According to Henry Swan Dana’s History of Woodstock, the toll gate that was originally about 3 1/2 miles from Woodstock’s court house was moved to the area where the two roads shown on this map intersected. This move occurred around 1806-1808. Dana notes that although the travellers from North Bridgewater, Barnard, and other nearby areas had to then pass by the toll gate, tolls were not collected from these travellers until 1838. © Woodstock History Center
With David Bosworth now in charge, a toll was assiduously collected from everyone, except those travellers who were going to meeting, the mill, or were on military duty. The previous exclusion of people attending to “family concerns” was dropped as Mr. Bosworth claimed he did not understand the meaning of the term “family concerns,” even though such wording was in the charter. Bosworth began demanding a toll of all those drawing wood, or going to get their horses shod, or going to Woodstock to trade.
Many of the local people protested saying that they used the toll road only from the bridge at Vale Center to the village of Woodstock, and therefore they should only pay for the portion of the road that they used. Mr. Bosworth remained resolute in his interpretation of the toll collection policy.
The solution of how to get around paying the tolls was an easy one. Local businessman and town leader General Lyman Mower soon laid out a short road to circumvent the tollbooth. This new little road, which turned off to the left above what was then Mr. Thompson’s house (present-day Bassett Farm) and then followed along what is now Route 12 to the “Old Sarah Maxham home,” was called the shunpike because it provided a way for many of the travellers to shun, or avoid, the toll booth section of the Turnpike.
General Lyman Mower. © Woodstock History Center
The Shunpike
The above detail is from an 1856 map of Woodstock. It shows the location of the Thompson place (current Bassett Farm), Mrs. Dana’s house (near base of Mount Tom), and the Levi Benson’s House (which was the toll booth operated by Mr. Bosworth). What was formerly the “shunpike” is now part of Route 12N. The southern part of the Royalton and Woodstock Turnpike that runs from Pomfret to Woodstock is now called “Pomfret Road.” © Woodstock History center
The Royalton Woodstock Turnpike Company responded to the construction of this shunpike by moving their toll gate from Willow Vale Center some seventy rods closer to the Village, to the area near the base of Mt. Tom. Thereby insuring that travellers couldn’t easily bypass the tollgate without paying a toll.
Next to this toll gate, the Turnpike Company constructed what has been alternately described as a “caboose” and a “little temporary hut in the bank” for the gate keeper’s accommodations at this site. Many of the locals were clearly angered by the location of the new gate, and within five days of its completion, the little building that served as the tollgate keeper’s accommodations was blown up by some townspeople who had placed an explosive device in the “caboose’s” stove.
David Bosworth, the man in charge of this section of the Turnpike, was not a man with whom to trifle. He remained undaunted. He had a small building constructed and set up in the same general area as the “caboose”, but a little closer to the village, and he installed himself as the new gate keeper. It appears from various sources that several skirmishes then occurred, one of which was related by Henry Swan Dana, author of History of Woodstock, who writes: “It was while Mr. Bosworth was stationed here as gate keeper that two of the town authorities of Woodstock invaded his premises, with the intent to remove that gate. Mr. Bosworth, who was a man of stalwart proportions and physical strength to match, on learning the errand of his visitors, resisted the process, and with such effect that his invaders were completely overthrown in the ditch. He then went on further to remark to the authorities, as they picked themselves up and walked off: “I have no objections to your taking away the gate, if only enough of you’ll come.”
Occurring during this same period of overt contention, in the late summer and early fall of 1838, a concert was then advertised to be held at the toll gate and loyal citizens were encouraged to bring both their voices and their arms to insure that the gate was removed. The event might have led to a scuffle; however, Titus Hutchinson, a noted Woodstock lawyer and judge, weighed in advising people to pay the money that is demanded for the tolls, but then bring a suit against the toll collectors if they felt the tolls that they were being charged were unlawful.
At that “concert” apparently the gate was left in tact and David Bosworth collected the tolls.
While Mr. Bosworth won that battle, he did not win the war. Interested parties in Woodstock decided to seek a legal solution. A year later, in October of 1839, Vermont’s State legislature passed a bill granting the courts to take over real estate “when in their judgment the public good requires a public highway.” A decision was then made to lay a new road, that could be used for free, over the existing Royalton-Woodstock Turnpike which had run from the Meeting-house in Royalton to the Courthouse in Woodstock. Despite protests from David Bosworth and the Turnpike Company, the new public road was opened in 1842.
Pay the toll!
One of the many inconsistencies with the story of the Turnpike is raised by the above article, which was found in the September 7, 1838, issue of the Vermont Mercury. According to Henry Swan Dana’s History of Woodstock, the “concert” to remove the tollgate was to be held in the latter part of September of 1838. Dana states: “September 17, 1838, the town instructed the selectmen to remove the gate and tollhouse from the road near Daniel Dana’s, and to employ a sufficient force for that purpose at the expense of the town. In obedience to this order the selectmen removed said gate the next day, but it was set up again. Placards were then posted about the streets of the village and along the highways, advertising a concert to be held forthwith at the toll-gate, and warning all loyal citizens to be present and assist with their arms and voices.” In contrast to Dana’s timeline of events, the above advertisement, dated August 29, 1838, appears to to suggest that the failed “concert” took place in August.
As a side note, in many cases, likely including the Royalton-Woodstock Turnpike Company, the turnpikes proved not to be the great money-making investment that early investors believed they would be. There are several reasons for this. First, the building of roads was extremely expensive. In many cases, the turnpike companies tried to build straight roads without regard to the terrain. This meant that roads were built in places that were extremely steep or not easily buildable for other reasons, and this added to construction costs. Second, the issue of people not wanting to pay the tolls and the rise of shunpikes meant that it was difficult once the roads were built to recoup income from them. Lastly, as anyone who lives in Vermont knows, roads have to be constantly maintained. It is likely that the turnpike companies, having built the roads, realized that the cost of continual maintenance would likely eliminate most, if not all, of the profits.
As for the little house in which Mr. Bosworth had stayed when he served as the toll collector -- -- it was eventually moved across the road and became the residence of Levi Benson, who lived in it the rest of his life. Based on various documents, it appears that part of the back part of the house that is located near the Mount Tom parking lot contains part of this old tollbooth.
The other toll booth that had originally been built in Vale Center in 1852 was moved to the area near the base of Mt. Tom and became the home of a Mrs. Dana. According to an article published on June 1, 1899 in the Vermont Standard, this tollbooth was built near the toll gate in Willow Vale Center about 1818. The building served as a home to James Raymond and his family although it is not clear from the article whether this building was used as the Raymond’s domicile while it was operating as a tollbooth or during the period that followed the tollgate’s removal to the area near the base of Mount Tom.
In the Vermont Standard article, it is written, : “This house [the tollbooth] as we first remember it was occupied by James Raymond and family, consisting of wife and five children. Uncle Jim, as he was usually called, was a brick mason by trade, and if you chanced to know him would never forget his originality. His wife was one of of the largest women of her day and generation. I can see her as if yesterday, travelling across the well-worn kitchen floor, which bent and squeaked at every step. There are many incidents connected with the family and toll-house which I give but a passing notice. The good wife had more than once told Uncle Jim that some day there would be a big hole in the kitchen floor and she in the cellar. His reply was that it always had held, and he guessed it would. The prophecy proved true, for not many days after she and one of the girls suddenly found themselves as far down as the potato bin, much more frightened than hurt.”
The possible location of the old tollbooth on the Barnard Road.