Columbia Turnpike, now known as Route 23, connected the farms in the eastern part of Columbia County with Hudson and the river. Two toll houses, both listed in the National Register of Historic Places, survive at either end of the turnpike: East Gate in Hillsdale and West Gate in what is now Greenport. (Columbia Turnpike was established before the secession of Greenport in 1837, so West Gate was originally in Hudson.)
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| East Gate |
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| West Gate |
Built during what the History of Columbia County, New York (1878) called the "era of turnpike roads," the Columbia Turnpike was meant to link New York farmers near the Massachusetts border with the Hudson River. The History goes on to state that the Dutch settlers in the area were originally against the construction of such a road, because they believed that if their grandfathers didn't need one, then they wouldn't either. It is thought, however, that New Englanders were able to assert their influence, and since there were settlers from out east in the town of Hudson, and New England was just past the Taghkanic Hills, "a turnpike-road between these two points was inevitable." The turnpike was chartered in 1799 and stretched through six towns, covering 20 miles, and it is stated that the first toll was taken in November of 1800.
The West Gate Toll House is made of stone, but the East Gate Toll House is wood and consequently was more vulnerable to modern-day hazards in its location close to the road. In 2023, approval was obtained to move National Register-listed building thirty feet to protect it from traffic and road hazards.
Yesterday, Friends of East Gate made the following announcement about the progress in reconstructing and preserving the East Gate Toll House:
Friends of East Gate announced today that reconstruction of the historic East Gate Toll House will enter a major new phase in early April, when the building's original early 19th-century timber frame will be mounted onto its newly completed foundation along NYS Route 23, just west of the Massachusetts border in Hillsdale.
Motorists traveling along Route 23 this spring will be able to witness the long-anticipated reassembly of one of few surviving tollhouses in New York State—a visible milestone in a preservation effort that began nearly a decade ago.
Friends of East Gate was established in 2016 with a mission to save the East Gate Toll House from collapse and restore it as a landmark of early American transportation history when the building was added to the National and New York State Registers of Historic Places. Since then, the structure has been carefully investigated, stabilized, and supported to prevent further deterioration.
Constructed following a 1799 act of the New York State Legislature, the East Gate Toll House served travelers on the Columbia Turnpike, a toll road organized by the founders of the City of Hudson—known as the Proprietors—that connected the Hudson River to the Berkshires. The East Gate was one of three tollhouses along the route.
Given the structure’s fragility, it was carefully dismantled to preserve its historic fabric. Its original timber frame and many salvageable materials were documented and safely stored for reuse. A new foundation was constructed in 2025—safely set back from the roadway—preparing the location for reconstruction.
The historic timber frame will be raised and secured onto the foundation by Babcock Timber Framing of Lanesborough, Massachusetts, marking the moment when the building will once again stand along the historic turnpike corridor.
Work will continue throughout the spring and summer to restore the exterior structure. Additional fundraising will be required to complete the building’s historic details and interior, ensuring that the tollhouse can serve the community as an educational and cultural resource.
“This is the year the East Gate Toll House gets back on its feet,” said James Wagman, chair of Friends of East Gate. “After years of planning, stabilization, fundraising, and careful preparation, the public will finally be able to see this historic structure rise again in the landscape where it stood for two centuries.”
The reconstruction represents a significant step in preserving regional history and the legacy of the Columbia Turnpike—one of the earliest transportation corridors linking local farms and industry to Hudson River markets—and restoring a rare surviving example of vernacular toll house architecture.
“Reconstruction is only the first step,” Wagman added. “We are now beginning the search for a responsible tenant—ideally a nonprofit or low-impact business—that will help sustain the building, support public interpretation of its history, and ensure its long-term vitality.”
To learn more about the project and the vision for this historic structure, visit friendsofeastgate.org.


















