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.

Helmsley is situated on the River Rye on the A170 road, 14 miles (23 km) east of Thirsk, 13 miles (21 km) west of Pickering and some 24 miles (39 km) 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. The town is a popular tourist centre and has won gold medals in the Large Village category of Yorkshire in Bloom for three years. The town square is a meeting place for motorcyclists as it is at the end of the B1257 road from Stokesley, which is a favourite with bikers.

The Cleveland Way National Trail starts at Helmsley, and follows a horseshoe loop around the North York Moors National Park and Yorkshire coast for 110 miles (180 km) to Filey. The remains of Helmsley Castle, which was destroyed in the Civil War, loom over the town.