Dog-friendly Helmsley

A family-run inn straight on Helmsley market place, a minute from the castle and the start of the Cleveland Way. The owners state plainly that they are dog friendly, and it is a reliable first pint at the end of the walk in from Rievaulx.

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.

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.

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.

A four-star coaching inn spanning a Tudor rectory and Georgian townhouses on Helmsley's market square, now part of the Inn Collection Group and so dog friendly it has its own hotel Labrador. Up to two dogs stay for fifteen pounds a night in designated pet-friendly rooms, and dogs can join you in set areas of the pub and restaurant. The castle, walled garden and Cleveland Way start are all on foot from the door.

A stone coaching inn on Helmsley's market place whose Pickwick Bar holds the longest single piece of Mouseman oak Robert Thompson ever made. Dogs are welcome in the bar and a separate restaurant area, dog-friendly bedrooms come with a doggy welcome pack (fifteen pounds per night, up to two dogs), and pet-friendly dining tables can be requested when booking. A relaxed, unstuffy base for Rievaulx and the moors.

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.