Route diagram, drawn from the recorded track — for the shape of the walk, not for navigation. Carry OS Explorer on the hill.
The opening leg of the Cleveland Way, from the Cleveland Way car park in Helmsley through fields and bluebell woodland into the deep pastoral valley of the Rye, arriving at the soaring ruins of Rievaulx Abbey - around three miles each way, or up to seven miles as a circuit. Dogs can stretch out off lead through the wooded sections but must go on lead past the sheep fields at the start and on the abbey grounds, where leashed dogs are welcome in the ruins and cafe. One of England's great short walks, with a monastic masterpiece at the end.
An easy 4.5-mile loop with 100 metres of ascent, under two hours, running out of town along the grass terraces of Duncombe Park and down the stepped Fairy Staircase to the River Rye; smooth going apart from the steps, which are steep and greasy in the wet. Start at Helmsley market place, five minutes from the castle car park, and the town is well served by buses from Thirsk, Malton and Scarborough. There is deep water in the Rye for a swim and shade from the veteran parkland oaks, but Duncombe Park is a working estate and a national nature reserve, so dogs stay on the lead throughout and off the deer lawns.
A country house hotel and spa a step off Helmsley market place, with a heated outdoor pool and gardens. A set number of bedrooms take dogs by prior arrangement, and extra towels for wet paws are available from reception.
The gaunt split keep and deep earthworks of a twelfth-century castle, right at the edge of Helmsley market place. English Heritage lists it among its dog-friendly properties, so a lead-length tour of the ramparts is easily fitted around a walk on the Cleveland Way.
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