NY 277 begins at an intersection with NY 391 (Boston State Road) in the hamlet of North Boston (in the town of Boston). Running northeast along Herman Hill Road, NY 277 is a two-lane local road, passing the North Boston Stadium, crossing a junction with South Abbott Road (County Route 28 or CR 28) before becoming a dense woods road into the town of Orchard Park and changing names to Boston Ridge Road. Returning to a residential road, the route turns eastward south Chestnut Ridge Park, reaching a junction with Chestnut Ridge Road (CR 552), where NY 277 turns northward.