Helmsley is situated on the bank of the River Rye lying on the southern edge of the North York Moors National Park. First recorded in 1086 as a village with three manors, Helmsley is now one of the most popular of Yorkshire’s market towns.

Helmsley Castle is regarded as a fine example of a medieval castle building. The civil war saw the destruction of the castle in 1644, during a three-month parliamentary siege led by Parliamentarian Sir Thomas Fairfax. At the beginning of the 18th century Duncombe Park, a magnificent stately home with wide expanses of gardens and parkland, was built for Sir Charles Duncombe.

Pickering is a popular tourist centre and the largest of Ryedale’s market towns. Reputedly founded in 270 BC by King Peredurus, the ancient king of the Brigantes, Pickering may well be one of the oldest towns in the area. During Norman times a motte and bailey castle was built in the town and is now cared for by English Heritage. The outer Barbican wall of the castle was built by Edward III in anticipation of trouble resulting from the Battle of Byland some 18 miles away.

The church of St Peter and St Paul whose 14th century spire is visible from miles around, contains remarkable examples of 15th century murals depicting biblical scenes.

A market town of unspoilt, old-fashioned houses and fine inns, Kirkbymoorside, meaning ‘church by the moorside’, was built around a church on the edge of the moors.

The heyday of the town came in the Georgian period when fine houses were built in the ‘Ends’ and in Church Street. The town became virtually self-sufficient and milling, brewing and linen manufacture were dominant.

A by-pass now takes traffic past the town, but it is worth a detour to discover a gem of the moorland fringe.

The towns of Malton and Norton stand on the banks of the River Derwent. They have been the historic centre of Ryedale since Roman times, when a 22 acre legionary fort - Deventio, was established in AD70.

Malton and Norton thrived through the ages and became the focal point for the local agricultural community, the brewing industry and for the race horse training fraternity. The towns are both centres for horse racing and are often referred to as ‘The Newmarket of the North.’ Thoroughbreds are often seen on their way to and from the gallops on Langton Wold.

North of the Roman Fort site is the original town of Old Malton, with ancient stone houses and the beautiful St Mary’s Church, which is built around an old Gilbertine Priory, making it the only Gilbertine Priory in use in England.

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