Thoughts on the East Gate Toll House

Have you ever come upon a problem that caused you to feel stumped? You’re not alone.

In the latter part of the 18th century, the young United States was hobbled by horrendous roads, which made it difficult or even impossible for farmers and manufacturers to move goods to market. American roads at the time were rough and unreliable, often no more than obstacle courses hacked out of the wilderness.

Farmers in Berkshire and Columbia Counties faced the problem of transporting their produce and livestock to the Hudson River for shipment to the rapidly expanding New York City metropolis. They would load their goods in wagons and follow a crude cart path that traversed the county from east to west. The path was created in what was then virgin forest: it was nothing more than two ruts in the dirt, punctuated by 18-inch tree stumps woodsmen left behind after felling the trees to clear the path. The tree stumps were just low enough for a wagon to clear.

That is, if the weather was dry. When winter snows melted and spring rains turned the path into a muddy morass, wagons would sink down into the muck, get caught on a tree stump, and leave the unlucky farmer to wonder how he’d get out of the predicament. It was called being “stumped.”

A 1799 act by the New York Assembly authorized the creation of the Columbia Turnpike Corporation for “improving the road from the city of Hudson to the line of Massachusetts, on the route to Hartford.” The corporation sold shares of stock to finance the construction of the Columbia Turnpike. Before the Civil War, the turnpike took the easiest course, which resulted in the development of mills, tanneries, blacksmith shops, taverns, and post offices in Hillsdale, Bain’s Corners (Craryville), Hoffman’s Gate (Martindale) and Smokey Hollow (Hollowville). Today, the turnpike follows Route 23/23B.

Three toll houses were built: West Gate, a handsome limestone building still standing in Greenport on Rt. 23B; Middle Gate, once in Martindale near the Taconic Parkway but now long gone; and East Gate, a wood frame building just east of Mitchell Street in East Hillsdale. Tolls collected at these toll houses paid for the upkeep of the turnpike and the passage to the river became much easier.

Even so, some farmers shunned paying the tolls and carved out a crude path to avoid East Gate. It was aptly called Shun Pike Road, a name it retains to this day.

The toll houses remained in operation until 1907, when the county bought the rights from the Columbia Turnpike Corporation. East Gate became a private residence and was occupied by at least two generations of the Decker family, after which it was acquired in 1970 by Eldena Jenssen who dreamed of rehabilitating the place.

In 2016, the East Gate was placed on the State and National Historic Registers, and a group of local residents came together to consider how this important artifact in the social and economic development of Columbia County could be rescued and restored.

The first step was to acquire the toll house, but how to finance the purchase left the committee, well, stumped. That’s when Copake Falls resident Edgar Masters stepped up and made a donation that allowed the purchase of the toll house and the Friends of East Gate (FoEG) was born. The first order of business was to get an engineer into the toll house to assess what is needed to stabilize and weatherproof the building. Since no tax dollars will be used to finance the work, the FoEG must rely on private donations. Just when we thought we would be stumped again, a donor generously contributed the funds to start Phase I of the work. If you would like to contribute to the restoration of this important part of Roe Jan history, please visit

The Friends of East Gate will seek input from the community about how the restored East Gate toll house can be a community resource in the future. In the meantime, there’s an exhibit at the Roe Jan Historical Society this summer, “All Roads to the River” with a lot of rich historical information about the role the Columbia Turnpike played in the development of America in the early years of the Republic, and a replica of the original toll gate! Don’t miss it!

And if you have noticed the banners hanging on the East Gate toll house and wondered about them, we hope this post keeps you from feeling stumped!

Recent Queries:

A Rochester, NY, man is researching the Davis family. Specifically, he is looking for information about the parents and siblings of Calvin W. Davis (1816-1901). He has visited the Pill Hill cemetery and found the grave of Elisha Davis, who may have been Calvin’s father. Elisha was married to Batesy Davis. If you have any Davis ancestors or know someone who does, please let us know.

A Hillsdale resident is researching the old post office on Anthony Street. There is some confusion about the date of its construction (1945 or more likely the turn of the century) and when the building, which was built at ground level, was raised onto a new foundation and why. Any information would be appreciated.



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6 Responses to Thoughts on the East Gate Toll House

  1. James Wagman says:

    Great Blog!! Keep it up!

    Liked by 1 person

  2. Susan Closson says:

    This was very interesting. What about making it a museum after it is repaired and safe to enter? There could be pamphlets and a historian for talks to the children of this area. If the schools in the area attended a field trip maybe even small snack based on the food they would have eaten at that time in life. Possibilities are endless.

    Liked by 1 person

  3. Danielle Camacho says:

    As an educator I love that idea. Since I was young I wanted to see the toll House revived and I am so glad it is happening. If there are any non-monetary ways we can donate, please let us know.

    Liked by 1 person

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