1750-1790s
Mountains, streams and thick forests made the interior of New York State difficult to reach. In 1753 Catskill explorer and pioneer, Gideon Hawley described the landscape as “obstructed by fallen trees, old logs, miry places, pointed rock and entangling roots.”
Gideon Hawley as quoted by Seymour Dunbar in A History of Travel in America
As European settlers pushed farther westward in search of more land, they made their way down the Susquehanna River, following trails made by Native Americans and marks on trees made by the few settlers that had gone before them.
After the Revolutionary war, there was an increase in westward migration, creating a need for new and better roads as the existing trails were not wide enough to accommodate wagons. In response, NYS attempted to improve existing roads using money raised from lotteries. In August 1790, hired by the State, Surveyor C. Gelston set out to map and evaluate the condition of a route from Wattles Ferry on the Susquehanna River to Catskill on the Hudson River by way of Windham.
The lotteries failed to raise sufficient funds and the State turned to chartering turnpikes, roads owned and maintained by private companies, instead.