Built in 1815 to overcome a lack of transportation when the Hudson River froze during the winter months. To resolve the issue, in 1815, the Philipstown Turnpike Company was organized to improve upon a toll road from Cold Spring to the Connecticut border. On April 15, 1815, "an act to incorporate the Philipstown turnpike company in the county of Putnam" was passed.
East of the Connecticut border, the turnpike continued as the New Milford and Sherman Turnpike.
On the turnpike, wagons transported manufactures inland, and carried produce from the eastern part of the county. Before the advent of the railroad, the road was a business center for much of the county. One of the intentions of the turnpike was to "greatly promote the public good, as well contribute to their individual interest". However, the turnpike was eventually abandoned, because the tolls received were not sufficient to defray the expense of maintaining the road and associated bridges.