NY 21 turns north onto South Main Street, following NY 332 through the city's historic downtown district.
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While NY 15 continues north from the village into Livingston County, NY 21 leaves Wayland on an east–west alignment, roughly paralleling the northern county line and a B&H Rail Corporation line as it runs through a valley surrounding the Cohocton River.
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The two routes pass by 426 South Main Street, Benham House, and the city's former United States Post Office, all properties listed on the National Register of Historic Places, before splitting at the junction of Gibson and North Main streets.
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