Route diagram, drawn from the recorded track — for the shape of the walk, not for navigation. Carry OS Explorer on the hill.
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.
A restored five-acre Georgian walled garden beneath Helmsley Castle, run as a horticultural charity, with orchards, hot borders and glasshouses. Well-behaved dogs on leads are welcome throughout, including the shop and plant centre, and dog biscuits and water are laid on - the Vine House cafe within the garden is dog friendly too. A gentle, sheltered hour that slots neatly into any Helmsley day.
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