The Roeliff Jansen Historical Society
PRESERVING THE HISTORY AND HERITAGE OF THE ROE JAN COMMUNITY

Copake Falls circa 1900
Our Next Site Visit:

Columbia Turnpike and Toll Gates
Presentation with Peter Cipkowski - including a brief Site Visit to East Gate Toll House on Rte. 23 in Hillsdale
Sunday, August 23, 2026
After the Revolutionary War, New York City's population surged, creating a steady market for farmers in what is now Columbia County. However, getting goods down to the city meant hauling them west over rough roads to the Hudson River and the port city of Hudson, a city that had been chartered in 1785.
In 1799, the New York State Legislature authorized the creation of the Columbia Turnpike Corporation for the purpose of improving the road from the city of Hudson to the line of Massachusetts on the route to Hartford. When the Columbia Turnpike was constructed, it was the first turnpike in Columbia County and the fifth in New York State.
The legislature also gave rights to the corporation to use existing roads and approved the construction of three tollhouses spaced about 10 miles apart. The revenues from the tolls paid by travelers covered the cost of construction and ongoing maintenance of the turnpike.
The word 'turnpike' came from the use of heavy wooden pikes swung aside by toll keepers after payment was made. As part of our exhibition programming, historian Peter Cipkowski will give an illustrated talk about the Columbia Turnpike and the two surviving toll houses, Westgate in present-day Greenport and East Gate in Hillsdale, currently being restored. The former Columbia Turnpike is essentially today's routes 23 and 23B.
Following the presentation, participants will have the option to visit the actual East Gate Toll House on Rte. 23. Since parking is limited at the site, carpooling is recommended for those wishing to go (we will assist with carpooling arrangements on the day).
In another presentation scheduled for 2 pm, Sunday, September 13, Hillsdale historian Chris Atkins will describe his extensive research to determine the location of the long-lost third toll house known as Middle Gate, which disappeared sometime after 1907 when the Turnpike closed. The presentation will take place at the Roeliff Jansen Historical Society, 8 Miles Road in Copake Falls, NY.
(Below, a graphic by Peter Cipkowski illustrating the route of the Turnpike & locations of the three toll houses)
THE VIDEO - The Columbia Turnpikes and Toll Gates Chapter
Written and narrated by Lesley Doyel, edited by Nick Fritsch
(Running time is a little over 2 Minutes)
This chapter of our exhibition overview features the Columbia Turnpike, authorized by the New York State Legislature in 1799 to improve the route from Hudson to the Massachusetts border and onward to Hartford. It was the first turnpike in Columbia County and the fifth in New York State, and was financed by tolls collected at three tollhouses spaced roughly ten miles apart. Running time is 2:13

