Helmsley is an attractive market town, the only one in the North York Moors National Park, thirteen miles west of Pickering and twenty four miles north of York. A charter to hold a market was granted by Robert de Ros, in 1191. It is a popular tourist centre and a good touring base for walking, cycling and other open air activities. It has retained its basic medieval street plan, centred on the Market Place. The town prospered after the founding of nearby Rievaulx Abbey in 1132. The linen weaving industry was very important to Helmsley in the 18th century. It was undertaken along the Borough Beck, as water was needed for the process. Dyer’s Bridge, behind the Town Hall, takes its name from the industry. Dying was carried out downstream from the bridge, to avoid pollution in the town. The centre of Helmsley has been designated a conservation area. Many buildings date from the early 17th century. The River Rye runs south of the town, where it is joined by the Borough Beck, flowing off the moors.
Helmsley is well served by pubs, hotels, shops and teashops, many of which are in the Market Place. Hunters of Helmsley is a family run delicatessen which was the winner of the UK Best Small Shops Competition in 2015. The Beck Tea Room in Castlegate, is a popular, long established tea room. It is owned by local farmers and serves, where possible, locally sourced food.
The Royal Oak Hotel is a family run pub, with a welcoming and relaxing atmosphere. It has five en-suite rooms. The Black Swan Hotel, which also has The Tearoom, offers accommodation in forty five guest rooms. Although The Feathers Hotel only opened in 1959, the buildings date from the 18th century. Two private houses, previously owned by the Duncombe Park Estate, were converted by Jack and Peggy Feather into the hotel, hence the current name of The Feathers Hotel. The main building was previously a private house, occupied by a succession of doctors and their families. The other cottage, which is now the public bar and dates from 1780, was used by three generations of market-toll collectors. With the popularity of walking in the countryside around Helmsley, all three hotels are dog friendly.
The ruins of Helmsley Castle are an imposing sight. The castle was positioned on a natural rock outcrop, which dominates the area and controlled crossroads and a river crossing. This Norman castle was built in the early 12th century by Walter Espec, who also founded nearby Rievaulx Abbey. During the English Civil War, the castle was under siege for three months before Cromwell’s men successfully attacked it and left the Great Keep in ruins. It is now under the protection of English Heritage.
All Saints Church, in the centre of Helmsley, is a Grade II Listed Building. It dates from before the Norman Conquest and the churchyard was used as a market place in Anglo-Saxon times. It underwent much rebuilding in the 19th century.