At Willsboro, Route 22 heads to the northwest again, away from the lake, until it heads west and intersects US 9 in the town of Chesterfield, the other major north-south surface route up the state's eastern side.
NY 22 runs along South Catherine Street for a few blocks, then divides into one-way couplets for the first time since Westchester County, with northbound traffic moving a block to the east to follow Oak Street, while southbound traffic comes down North Catherine Street.