Talk about going from hither to yon and all places between! White Plains, Greenwich, South Salem, Carmel, Pleasantville, Tarrytown on great cycling roads. Yet you are never very far from a train station. Go for it and cycle to and from the start! Just allow enough daylight to get the job done.
Lots of turns. On and off roads. Sections of hardpack and trails. 25m tires and up recommended.
Pack a lunch!