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.
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.
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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