The portion of Route 199 east of its junction with the Taconic State Parkway was originally part of the Ulster and Delaware Turnpike, a toll road linking Bainbridge to Salisbury, Connecticut.

When the four-lane freeway section of the latter road reaches the cloverleaf interchange with US 9W, in the town of Ulster, between Kingston and Lake Katrine, it assumes the 199 designation as it continues eastward through woodlands.

It joins that highway northbound, immediately entering the town of Red Hook, for a two-mile (3.2 km) stretch through woodlands, first heading northwest then due north.

After crossing the Lakes Kill a thousand feet (300 m) further on, the road starts a long turn southeastward past the former Sky Park Airport and Red Hook Golf Club.

[7] The Saw Kill crosses again just north of the end of this section, at the small hamlet of Rock City, where the towns of Red Hook, Rhinebeck and Milan meet.

State Route 308 has its eastern terminus here, and a signal over the third crossing of the Saw Kill regulates traffic as NY 199 makes the abrupt turn eastward again.

A mile and a half further it resumes heading east,[9] past Milan's town hall, to its interchange with the Taconic State Parkway,[10] climbing slightly.

After crossing Ham Brook, the highway turns north northeast for three-quarters of a mile (1.1 km), bending back to the southeast around the side of an unnamed hill.

[12] The road returns to an east southeast heading as it descends another mile and the hills abruptly give way to more level ground on the outskirts of central Pine Plains,[13] where NY 199 passes Stissing Mountain High School and becomes West Church Street, still trending south.

Just past Pine Plains' town hall, at Hammertown, NY 82 turns north, towards the Columbia County hamlet of Ancram, ending the concurrency.

Three miles (5 km) of long curves in a generally eastward direction, climbing slightly, it reaches another small hamlet, Pulvers Corners, at an intersection with County Route 59.

East of Rhinebeck, the turnpike passed through the hamlets of Eighmyville, Milan, Lafayetteville, and Pine Plains and the village of Millerton on its way to the Connecticut border.