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. Off-lead information here is what walkers reported or what signage allows — never our advice. Whether and when a dog is off the lead is the owner’s decision and legal responsibility; keep dogs under control near livestock and follow signs on the day.
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.
Black Swan Hotel is a place to stay on Market Place, Helmsley. It is listed here so you know it is there, but we have not yet established whether dogs are welcome — so there is no verdict on this page and no stamp. If it is your business, claim the page and tell us, and we will stamp it.
Coopers of Helmsley is a place to eat on Bridge Street, Helmsley. It is listed here so you know it is there, but we have not yet established whether dogs are welcome — so there is no verdict on this page and no stamp. If it is your business, claim the page and tell us, and we will stamp it.
Crema Coffee House is a place to eat in Helmsley. It is listed here so you know it is there, but we have not yet established whether dogs are welcome — so there is no verdict on this page and no stamp. If it is your business, claim the page and tell us, and we will stamp it.
Real dog-welcoming cottages from our booking partner holidaycottages.co.uk — live prices, booked on their site. Booking through these links supports Wagfinder and never changes the price you pay.
Whisper Cottage
Yorkshire · dogs welcome
7 nights from £520
Lavender Cottage Helmsley
Yorkshire · dogs welcome
7 nights from £521
The Cottage At Cross Holme Farm
Yorkshire · dogs welcome
7 nights from £646
Fern Retreat
Yorkshire · dogs welcome
7 nights from £679
Ferne Cottage Helmsley
Yorkshire · dogs welcome
7 nights from £685
Filly Homestead
Yorkshire · dogs welcome
7 nights from £689
The Old Tin School
Yorkshire · dogs welcome
7 nights from £703
Moor Farmhouse
Yorkshire · dogs welcome
7 nights from £912
The Velveteen Bath House
Yorkshire · dogs welcome
7 nights from £1,183
Dale View
Yorkshire · dogs welcome
7 nights from £1,193
Know one we have missed?
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