A western bypass of Suffern was designated as New York State Route 339 c. 1932; however, it became part of a realigned NY 17 in the mid-1930s.

It heads to the southeast as the Korean War Veterans Memorial Highway, crossing over the Ramapo River and the Metro-North Railroad's Port Jervis Line before following both into Suffern.

At the end of the overlap, US 202 continues south along Orange Avenue to the New Jersey state line while NY 59 forks eastward toward central Rockland County.

While in Spring Valley, NY 59 has an overlap with CR 35A for about a tenth of a mile and meets the Thruway at exit 14, with a pair of park and ride lots located at the interchange.

The route continues eastward into Nanuet, where NY 59 passes through a heavy commercialized area, crossing under NJ Transit/Metro-North Railroad's Pascack Valley Line.

Before its busy intersection with CR 33, NY 59 passes The Shops at Nanuet to its south and the Rockland Plaza to its north.

The route proceeds onward, passing Palisades Center, one of the largest shopping malls in the country.

Immediately after passing Palisades Center, NY 59 becomes a four-lane surface road and briefly enters Central Nyack.

Its charter was renewed multiple times throughout the 19th century, and it was designated as a toll road to help pay for its upkeep.

[6] The turnpike was turned over from the county to the state of New York on July 14, 1911,[6] and added to the state highway system as part of Route 39-b, an unsigned legislative route extending from Nyack (at Broadway) to Harriman via modern NY 59 and NY 17.

[18][22] A local company carried out work to convert the highway into a shopping center access road; however, Rockland County asserted that the town—and by extension the company—had no rights to perform this action.

NYSDOT tried to fix the worsening situation in 1995 when they reconstructed almost 3 miles (5 km) of NY 59 from the eastern border of Spring Valley to exit 8 of the Palisades Interstate Parkway.

[5] Shortly after the traffic problems in Nanuet were reduced, the focus was shifted to West Nyack where Palisades Center was being constructed.

This caused major delays for motorists when a bridge was constructed from NY 59 to Palisades Center south parking lot.

Integrated Corridor Management systems and Intelligent Traffic Signal technology were also installed on NY 59 to decrease travel times for Hudson Link buses going to and from New York City.

The study, taking place between Winter 2019 and Spring 2020, will investigate possible improvements to the road, such as new bicycle lanes and sidewalks.