A market town and civil parish in the Ryedale district of North Yorkshire, England It is situated on the River Rye. It lies on the A170 road, fourteen miles east of Thirsk across the notoriously steep Sutton Bank, which ascends the Hambleton Hills approximately half way between the two towns; it is also thirteen miles west of Pickering. The Cleveland Way leads out of the town past Helmsley Walled Garden into the North York Moors National Park. The remains of Helmsley Castle tower over the town.
The town is associated with the Earls of Feversham whose ancestral home Duncombe Park was built overlooking the castle. A statue of William Duncombe, 2nd Baron Feversham stands in the town's square.
Other nearby places of interest include Rievaulx Abbey and Helmsley Arts Centre, the home of the 1812 Theatre Company.
The Helmsley area was badly affected by flash flooding on the night of 19 June 2005.
The town is a popular meeting place for motorcyclists as it is at the end of the B1257 road from Stokesley, which is a favourite with local bikers.
The band One Night Only is from the town.
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