The direction of the highway remains unchanged as it continues past several horse farms and Winding Hills Park on its way to the town of Montgomery.

For the next two blocks, to Wallkill Avenue, the highway marks the northern boundary of Montgomery's other federally designated historic district, Academy Hill.

[4] Past the elementary school, NY 17K runs parallel to the nearby I-84 but remains undeveloped, with the odd house, store or side street breaking the woods.

[4] Much of the land here is owned by the county as part of its Farmers' Museum, which surrounds the Nathaniel Hill Brick House, an early settler's home still occupied by his descendants.

This created a four-way intersection with Stone Castle Road, which was itself slightly relocated to the west as part of the plan to protect the adjacent Colden Mansion Ruins.

[7] Not far to the east of this junction is the lone piece of Drury Lane not included in the new route,[4] which now ends in a cul-de-sac[7] but still carries the CR 54 designation south of NY 17K.

[9] Development along the highway begins to increase at this point as NY 17K directly intersects I-84 and runs along the northern boundary of Stewart Airport.

The Newburgh Auto Auction's vast parking lots are visible to the north while commercial hangars and the local Air National Guard base can be seen to the south.

The base's entrance road, secured with a series of concrete barriers since the September 11, 2001 attacks, marks the end of the airport property.

[4] The route continues on, passing north of the Orange County Choppers's headquarters just before it crosses over the New York State Thruway (I-87).

Originally, the state planned to eradicate this entrance/exit ramp altogether, but changed their minds at the last minute when it was determined the overpass over Route 300 was in exceptionally good condition.