Our drawing of the route — the shape of the walk, 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 low circuit round the foot of Roseberry Topping from the National Park car park at Newton under Roseberry, for anyone who wants the hill without the summit scramble. It goes up through Newton Wood, which is thick with bluebells in May, then contours across the bracken slopes of Roseberry Common before dropping back to the road. The National Trust's own access statement for the property states that all dogs are welcome and that livestock graze in some areas, so leads go on where you meet stock. The car park has toilets and space for fifty cars at £2.50 up to two hours and £4.50 over two hours, and it is full by ten on a fine Saturday.
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
Know one we have missed?
Local knowledge beats desk research every time. Name the place and we will check it properly — the venue's own policy, confirmed, then stamped and dated like every other listing.
One short email when we add places or a council changes its beach rules. No noise, easy out.
NO SPAM · UNSUBSCRIBE ANY TIME · WE NEVER SELL THE LIST
Wagfinder Members
ENTER DOG OF THE MONTH · RESTRICTION ALERTS · CANCEL ANY TIME