This road was reconstructed in 1919 and became part of NY 39, a highway extending from Poughkeepsie to Patterson by way of West Pawling, in the 1920s.

After passing through the hamlet of West Patterson, NY 292 turns northwest, crosses the stream once again, and enters Dutchess County.

Just north of the county line in the Pawling hamlet of Holmes the route intersects with CR 30.

Near Holmes, the highway heads due north and passes between two small ponds.

[3] The route continues onward, traveling north through a rural, wooded area of Pawling with little development before curving west to pass along the southern edge of Whaley Lake.

[8][9] The route remained unchanged until January 1, 1970, when NY 216 was truncated to its current eastern terminus in Poughquag.