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.
The full 10.7-mile village round with 390 metres of ascent and about five hours, linking Cliff Ridge Wood, Newton Wood, the summit of Roseberry Topping and the moor traverse to Captain Cook's Monument before dropping back by Little Ayton; the final pull to the summit is rock steps and the descent off Easby Moor is steep. It starts at the High Green in Great Ayton, which has free short-stay parking and a long-stay car park on Station Road, and Great Ayton station on the Esk Valley line is a five-minute walk from the green. There is water in the River Leven at the start and in the woodland becks, and the woods are superb off-lead ground, but the summit has genuine unfenced drops on its north face, sheep graze Roseberry Common, and leads are required on the open moor from 1 March to 31 July.
Bridge Guest House is a place to stay in Great Ayton. 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 short, steady climb from the free Gribdale Gate car park up through larch woods to the 60-foot obelisk of 1827 on Easby Moor, raised to the explorer who grew up in Great Ayton below. Views sweep to Roseberry Topping and across the Cleveland plain, and a longer circuit links both summits via the Cleveland Way. Popular with dog walkers, but livestock graze along the trail, so leads on at times.
A 7.9-mile circuit with 300 metres of ascent and about three and three quarter hours, taking in Roseberry Common, the woods above Hutton Village and the long moor-top return to the obelisk on Easby Moor; the moor sections are firm sandy track but the climb from Hutton Village is steep and stepped. It starts at the Dikes Lane car park below Roseberry Topping, which is small and free and full by nine on a clear Saturday, with the alternative being Gribdale Gate a mile and a half round the other side. Newton Wood and the Guisborough plantations are grand for a dog off the lead and there are streams to drink from, but Roseberry Common and Great Ayton Moor carry sheep all year and the whole moor holds ground-nesting birds between 1 March and 31 July.
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 Pond Cottage
Yorkshire · dogs welcome
7 nights from £802
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
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