Helmsley lies in a hollow in undulating open countryside, flanked by heather moor to the north and the rolling farmland of the [[Howardian Hills]] to the south. The flat lowland of the [[Vale of Pickering]] stretches eastwards from the town towards Malton. The [[River Rye, Yorkshire|River Rye]] runs by the town to the south where it is joined at Rye Bridge by the Borough Beck flowing southwards through the town from the moors. Meadows south of the Rye form an important buffer and create an attractive setting for the town from the southern approach.