 The origins of NY 28A date back to 1907 when construction began on one of several dams that would eventually create the Ashokan Reservoir, a water body built by New York City to increase its water supply. In the initial stages of construction, seven villages in the reservoir's dimensions were destroyed and 64 miles (103 km) of roads were taken out of service. The latter were to be replaced with 40 miles (64 km) of new roads and 10 bridges carrying the highways around the reservoir's perimeter. According to a 1909 court order, the roads and bridges would be built and maintained by New York City in perpetuity to ensure that the residents displaced by the new reservoir would not be permanently isolated. The city's Board of Estimate initially balked at the measure, citing the mandate as their primary reason for rejecting a June 20, 1913, request by the city's Board of Water Supply for $ 1.3 million (equivalent to $ 311 million in 2016) to pave the perimeter roads.
