southeast past a junction with the western terminus of NY 299. Continuing south away from the Shawangunks, the routes cross North Mountain Road and make a bend to the southeast, reaching a junction with CR 7 at the hamlet of Benton Corners. After Benton Corners, US 44 and NY 55 continue southeast through the town of Gardiner, reaching the hamlet of Tuthilltown and a junction with CR 9. Tuthilltown to the Mid-Hudson Bridge Paralleling the Shawangunk Kill, US 44 and NY 55 soon reach the Wallkill River and cross it into the small hamlet of Tuthill. After a short bend to the southeast, the routes enter the hamlet of Gardiner. Now known as Main Street, the routes cross through the center of the hamlet, crossing a junction with CR 19 (Sand Hill Road). Leaving the hamlet of Gardiner, the routes soon reach the hamlet of Ireland Corners, where they meet at a junction with NY 208. East of NY 208, the routes continue east through the rural sections of Gardiner before crossing into the town of Plattekill. Soon after, the routes reach the hamlet of Modena. In Modena, US 44 and NY 55 junction with NY 32 (Main Street) in the center of the hamlet. Leaving Modena, US 44 and NY 55 turn northeast through Plattekill, passing multiple residences and cross under the New York State Thruway (I-87). Just east of the Thruway, the routes cross the northern terminus of CR 13 and soon reach the hamlet of Ardonia. At Ardonia, US 44 and NY 55 turn northeast at a junction with CR 10 (Milton Turnpike). North of Ardonia, the routes cross into the town of Lloyd, soon bending eastward into the hamlet of Clintondale. Passing numerous farms west of Clintondale, US 44 and NY 55 cross a junction with CR 22 (South Street) and through the residential hamlet. The routes soon cross back into the town of Plattekill, passing multiple residences along an eastward stretch near the Pancake Hollow Brook. At the junction with Jenkins Lane, the routes make a dart to the northeast and east, reaching a junction with CR 15 (Tuckers Corners Road). Crossing past several ponds, CR 15 forks off again at the junction with Pancake Hollow Road before US 44 and NY 55 reach the hamlet of Baileys Gap. Just east of Baileys Gap, US 44 and NY 55 cross into the town of Marlborough,