It runs through some lightly populated regions along the state's southern border, from Central New York to the Catskills.

Yet due to its location it sees little traffic, although for much of its length it follows the route of a main 19th century thoroughfare, the Catskill Turnpike.

NY 206 was extended west to Whitney Point in the early 1940s; another extension in the late 1970s moved the route's eastern terminus to Roscoe.

East of Triangle, the road crosses the Chenango County line and enters the hamlet of Barnes Corners.

[3] Through the town of Greene, NY 206 remains a two-lane rural road, reaching the hamlet of Genegantslet at the junction with CR 2.

Becoming concurrent with NY 41, the route runs southeast through downtown Greene, crossing the Chenango River and changes names to Washington Street.

After I-88, the route turns south, paralleling the interstate until the intersection with East Keech Road, where it returns to a southeastern progression through the town of Bainbridge.

Turning southeast along Stockton Avenue, NY 206 leaves the village, continuing as a two-lane road into the town of Colchester.

The routes run along the southern shore of the Pepacton Reservoir until NY 206 turns southeast at Cat Hollow Road.

[8][9] The extension was partially reverted on January 1, 1949, as the route was cut back to Greene;[10] however, NY 206 was reextended to Whitney Point in the mid-1950s.

[13] On June 19, 2007, a flash flood along the Beaverkill River and some nearby tributaries along NY 206 near the highway's east end took several lives.