crossing into the town of Beekman. NY 55 continues southeast through Beekman, crossing through the rural sections of Dutchess County, soon reaching the hamlet of Poughquag. At Poughquag, NY 55 crosses a junction with CR 9 (Clove Valley Road). Through Poughquag, the route is mainly residential, soon bending southward then southeast along Whaley Lake Stream into a junction with the eastern terminus of NY 216. Just east of that junction, NY 55 meets CR 32 and parallels the Whaley Lake Stream through the town of Beekman. Paralleling an old alignment of itself, NY 55 soon reaches a junction with the northern terminus of NY 292 as it enters the town of Pawling. Pawling to the CT state line Now in Pawling, NY 55 continues southeast on a parallel of the Housatonic Railroad and the Whaley Lake Stream, bypassing the hamlet of Woodinville. After making a gradual bend to the southeast and soon to the east, NY 55 becomes more residential as it approaches the village of Pawling. The route soon parallels CR 69, which is disconnected at NY 55. The route then crosses over the East Branch of the Croton River and the Metro-North Railroad Harlem Line, passing south of the Pawling station, which is connected via CR 69. A couple blocks east of the tracks, NY 55 enters a partial cloverleaf interchange with NY 22. NY 22 and NY 55 become concurrent through the village of Pawling, passing the Dutcher Golf Course and bypassing the center of the village. Passing the Pawling High School at Reservoir Road, NY 22 and NY 55 leave the village of Pawling and continue north through the namesake town. Paralleling the tracks of the Harlem Line, NY 22 and NY 55 cross through the hamlet of Hurd Corners, junction with the western end of CR 68. Just north of CR 68, the routes cross the Appalachian Trail at the site of the Appalachian Trail station. Continuing north through the town of Pawling, the routes parallel the tracks and the Swamp River before crossing into the town of Dover. Through Dover, NY 22 and NY 55 become a residential two-lane road, passing the Harlem Valley-Wingdale station and the Harlem Valley Golf Club. The routes soon reach the hamlet of Wingdale, where NY 22 forks to the north while NY 55 heads northeast past Thomas J. Boyce Park. Following an old alignment of NY 22, NY