Requires Metro North to White Plains, then a ride up to Massachusetts followed by a long train ride back. The closest train from Sheffield is a 30 mile ride to Wassaic on the Harlem Valley Line of Metro North. These trains run no more frequently than every 2 hours. Dingle Ridge, Joes Hill and East Street are climbs. East Street ascends 4 miles beginning just where Rt 7 exits the route off Rt 4 in Cornwall Bridge. By starting in North White Plains you jump right into country miles, which is what this ride is all about.
Nearest Metro North railroad station to return is Wassaic.