At an intersection with CR 102 (Old Quarry and Starr roads), the highway enters Spawn Hollow, a local hamlet.

Past the bridge, the highway turns eastward and into the hamlet of Beckers Corners, where it intersects with U.S. Route 9W (US 9W).

The route bends several times in a highly developed region as it enters the community of Selkirk.

Not far to the north of the junction, NY 144 connects to the New York State Thruway (Interstate 87) at exit 22.

[3] The origins of NY 396 date back to the mid-1900s when the portion of the route east of modern US 9W was first improved to state highway standards.

In the early-to-mid-1920s, the state of New York acquired a road connecting the west end of SH 193 to Callanans Corners in the town of Coeymans.