Our drawing of the route, over road and path data from OpenStreetMap. It shows where the walk goes and what it goes through. It is not a survey and not a navigation aid — carry OS Explorer on the hill.
A serious 14.1-mile day with 300 metres of ascent and around six hours on the clock, following the Cleveland Way out of town before a long haul up Rievaulx Bank and a moor-edge traverse to Newgate Bank; the woodland zigzags are slippery in the wet and the return down Riccal Dale is rutted by forestry traffic. It starts at Helmsley market place, where the Cleveland Way plaque is set into the paving, and the Cleveland Way car park on Cleveland Way itself is the obvious long-stay spot with the Moorsbus and Scarborough & District 128 both calling in the square. There is water in the Rye and in Riccal Dale, and long stretches of forest track where a dog can properly stretch out, but the escarpment fields above Rievaulx hold sheep all year and the last mile back into town is on lane.
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.
Five and a half miles with 110 metres of ascent and about two and a quarter hours, using the parkland drives and the riverside path below the terraces rather than the well-trodden Fairy Staircase route; the ground is mostly firm, with one muddy dip near the ha-ha. Start at Helmsley market place and walk out past the castle to the park gates on Buckingham Square, or use the pay-and-display at the Cleveland Way car park if the square is full on a Friday market. The Rye is reachable at several points for a swim and the open parkland lets a steady dog off the lead, but Duncombe Park is a working estate with fallow deer and sheep, and the National Nature Reserve section asks for dogs under close control at all times.
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.
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