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Hillsdale’s Toll House joins State and National Register of Historic Places


HILLSDALE — Nineteen sites in New York State, including one in Hillsdale, have been recommended by the State Board for Historic Preservation for inclusion on the State and National Registers of Historic Places, Governor Andrew Cuomo’s office announced last week.

The Hillsdale site is known as the Columbia Turnpike’s East Tollhouse.

Governor Cuomo’s office said the 1830s-era building, which currently is vacant, served as the eastern most toll in a series of toll gates on the Columbia Turnpike, a critical transportation route from the Massachusetts border to its terminal point at the Hudson waterfront between 1799 and 1907. The Hillsdale Toll House was nominated by Historic Hillsdale and the Roeliff Jansen Historical Society.

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The Hillsdale Toll House in 2016. Photo by Lance Wheeler

“The Hillsdale Toll House is both architecturally and historically significant – humble as it is,” said Peter Cipkowski, Hillsdale Town Supervisor and President of the Roeliff Jansen Historical Society, in a press release. “It may have only been a toll-keeper’s modest house, but its part of a much bigger American story. For the first fifty years of the new Republic, before there were railroads, the turnpike system drove commerce between the Berkshires and the bigger markets up and down the Hudson River.”

The Columbia Turnpike established a viable commercial trade route to and from the City of Hudson, an emerging center of commerce in the early nineteenth century. It was the longest turnpike in the state. Known to travelers as the East Gate, the Hillsdale Toll House mirrored the West Gate, an impressive limestone Toll House located in the Town of Greenport that is already on the State and National Register of Historic Places. Like the West Gate, the East Gate had a small porch and gate over the road. According to records, a ladder was lowered and raised when the toll was taken. The gate was open from 9 a.m. to 9 p.m.

A sign displayed fees and other regulations and hung on the Hillsdale building. The original sign now hangs in the pub of the Red Lion Inn in Stockbridge, MA.

The Turnpike operated until 1907, when the company’s rights were purchased by the county. The Hillsdale Toll House was a private residence for two generations of the Decker family for many decades until it was acquired by Eldena Jenssen in 1970, mother of its current owner, Victoria Jenssen.

“The Toll House is a critical part of the story of Hillsdale and all of Columbia County,” said Lex Lalli, chair of Historic Hillsdale, a town committee that promotes the preservation of Hillsdale’s unique heritage. “We’re exploring how this fragile historical gem is not lost to us and remains part of our future.”

A presentation of the Turnpike’s history and exiting toll houses is scheduled for Sunday, April 10, at 2 p.m., at the Roeliff Jansen Historical Society Museum in Copake Falls. For more information, visit

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