Helmsley is a market town and civil parish in the Ryedale district of North Yorkshire, England. Historically part of the North Riding of Yorkshire, the town is located at the point where Ryedale leaves the moorland and joins the flat Vale of Pickering.
It is situated on the River Rye on the A170 road, 14 miles east of Thirsk, 13 miles west of Pickering and some 24 miles due north of York. The southern boundary of the North York Moors National Park passes through Helmsley along the A170 road so that the western part of the town is within the National Park.
The settlement grew around its position at a road junction and river crossing point. Helmsley is a compact town, retaining its medieval layout around its market place with more recent development to the north and south of its main thoroughfare, Bondgate. It is a historic town of considerable architectural character whose centre has been designated as a conservation area. The town is associated with the Earls of Feversham, whose ancestral home Duncombe Park was built overlooking Helmsley Castle. A statue of William Duncombe, 2nd Baron Feversham stands in the town's square.