Helmsley is situated below the moors at the western end of the Vale of Pickering. It lies within a Conservation area with the North York Moors National Park boundary running through the centre.From mediaeval times it has occupied an important site at a crossroads and on a crossing point of the River Rye. The older part of the town developed around a spacious market square and is now bordered on the west by the Castle; the south by the river; and the north and east by more modern areas of development. From the Market Place radiate Church Street/High Street to the north west; Bondgate to the east; and Bridge Street and Castlegate to the south, and these together with Ryegate and Pottergate form the residential part of the old town.

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