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 14.6-mile expedition with 440 metres of ascent and six and a half hours of walking, crossing the vale from Stokesley, climbing Roseberry Topping by Newton Wood and returning by Newton under Roseberry and the field paths through Easby and Tanton; it is a long day of contrasts, flat farmland then one sharp hill, and the summit ridge is exposed to any wind going. It begins in Stokesley town square with its free short-stay bays, though for a walk of this length the Station Road long-stay at Great Ayton is a better bet if you can split the journey. The lower half is farmland with sheep and cattle throughout, the woods above Newton are lovely off-lead ground with becks to drink from, and the north face of Roseberry is a genuine cliff, so short lead on the top.
Bexters is a place to eat in Stokesley. 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.
Brass Monkey Beer Boutique is a pub on High Street, Stokesley. 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.
A small tap room and micro-pub in the middle of Stokesley, all cask and craft and no fruit machines. Well behaved dogs are welcomed indoors as well as in the beer garden, and the owners say so in as many words on their own FAQ.
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.
Roseberry View
Yorkshire · dogs welcome
7 nights from £1,507
Birchwood Stable Cottage
Yorkshire · dogs welcome
7 nights from £428
Hawthorn Cottage Yorkshire
Yorkshire · dogs welcome
7 nights from £447
Prospect Lodge Halifax
Yorkshire · dogs welcome
7 nights from £453
Clover Cottage Osmotherley
Yorkshire · dogs welcome
7 nights from £479
Number 2 Bank Top
Yorkshire · dogs welcome
7 nights from £484
Havercroft
Yorkshire · dogs welcome
7 nights from £485
Whisper Cottage
Yorkshire · dogs welcome
7 nights from £520
Lavender Cottage Helmsley
Yorkshire · dogs welcome
7 nights from £521
Dove Cottage Old Malton
Yorkshire · dogs welcome
7 nights from £649
Know one we have missed?
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