It proceeds north–south through downtown, passing several blocks of commercial buildings and Paul D. Schreiber Senior High School ahead of a junction with Main Street.
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CR 101's southern segment begins at an intersection with Shelter Rock Road (CR 8) and Herricks Road near Herricks High School.
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The route continues on through Searingtown into the village of North Hills, where the homes give way to trees as it turns to the northeast and passes under the Northern State Parkway.
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In 1952, the New York State Department of Public Works laid out plans for a six-lane expressway in western Nassau County.
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