The first several miles of NY 149 in Washington County pass through isolated, rural areas as it curves to the north and south while following a generally east–west alignment. In West Fort Ann, the only community along the route between the county line and the village of Fort Ann, NY 149 intersects with Old State Route 149, a loop route of NY 149 that was created when the highway was realigned. The route continues east from the community, exiting Adirondack Park and crossing over Halfway Creek on its way into the village of Fort Ann, where it becomes Ann Street. Within the village, NY 149 passes the Fort Ann Cemetery and two blocks of homes before intersecting with US 4 at George Street. NY 149 turns to the south, joining US 4 along George Street through downtown Fort Ann. After passing the town park, US 4 and NY 149 leave the village and become nameless as they head south into the town of Kingsbury.