The portion of Washington Road and Washington Street from North Main Street in the
village of Pittsford to the modern junction of Panorama Trail and North Washington Street north of
East Rochester was initially constructed prior to 1900. North Washington Street continued northeast into the town of
Penfield, where it ended at Penfield Road west of the
hamlet of Penfield. On November 12, 1908, the state of
New York awarded a contract calling for the improvement of Washington Road between the Pittsford village line and Fairport Road. The long section of highway was accepted into the state highway system on August 15, 1909. The state let a contract to improve the section of Washington Street from Fairport Road to Penfield Road on November 4, 1915; it was added to the state highway system on January 9, 1917. s in
East Rochester that had been patched to read "153". When
NY 253 was assigned as part of the
1930 renumbering of state highways in New York, it ended at
NY 64 south of Pittsford. NY 253 was extended northward through Pittsford to Penfield along the Pittsford–East Rochester–Penfield state highway by 1936. The bridge carrying NY 253 over
Irondequoit Creek in Penfield was closed to vehicular traffic in the 1960s; as a result, NY 253 was rerouted north of the junction of North Washington Street and Linden Avenue to follow Linden Avenue eastward across Irondequoit Creek to Whitney Road in
Perinton. Construction on a new
divided highway for
NY 441 began in the late 1960s. As part of the construction, a four-lane extension of Panorama Trail was built to connect Panorama Creek Drive and North Washington Street to the new expressway. The new highway was completed by 1971 and named Panorama Trail South. The segment of Panorama Trail South from North Washington Street to the NY 441 interchange became part of a realigned NY 253; NY 253 was truncated southward at some point in the latter half of the 1980s to end at
NY 65 in the town of
Pittsford. The portion of NY 253's former routing from
NY 96 (North Main Street) in Pittsford to NY 441 in Penfield was redesignated as NY 153. For many years, signs along NY 153 were holdovers from the NY 253 designation, as evidenced by covered numbers on multiple shields and
reference markers along the highway. In 2007, ownership and maintenance of NY 942B was transferred from the state of
New York to
Monroe County as part of a highway maintenance swap between the two levels of government. A bill (S4856, 2007) to enact the swap was introduced in the
New York State Senate on April 23 and passed by both the Senate and the
New York State Assembly on June 20. The act was signed into law by Governor
Eliot Spitzer on August 28. Under the terms of the act, it took effect 90 days after it was signed into law; thus, the maintenance swap officially took place on November 26, 2007. The former routing of NY 942B is now part of CR 270, a route that continues northeast on Panorama Trail to Penfield Road.
Rehabilitation and reconstruction The portion of NY 153 south of West Commercial Street in East Rochester had not been substantially reconstructed since 1915. In mid-August 2007, construction began on a two-year, $3.2 million project to resurface and reconstruct NY 153 from NY 96 north to West Commercial Street. The project was divided into two sections, with
NY 31F (Fairport Road) acting as the divider. Work on the first section from NY 96 to NY 31F involved the resurfacing of the road and the elimination of the
slip ramp between NY 96 north and NY 153 north through the reconfiguration of the NY 96 / NY 153 intersection. Both were completed by late 2007. The second section of NY 153 from NY 31F to Commercial Street was entirely rebuilt. As part of the project, new sidewalks, curbing, and drainage systems were constructed along the roadway. During the course of construction, only one direction of traffic was allowed on the road. NY 153 northbound was closed first; travelers heading north were instructed to follow NY 31F, Lincoln Road and Linden Avenue to traverse the village. Construction paused in November 2007 for the winter months, at which time the highway was reopened to two-way traffic. From May 26 to June 28, both directions of NY 153 between NY 31F and Commercial Street were closed to traffic to allow for a larger scale of construction. The project was completed in October 2008. ==Major intersections==