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Stokesley · 3 checked

Dog-friendly walks in Stokesley

Boots on. These are the Stokesley walks worth the drive, with lead rules and livestock warnings marked.

WAGFINDER No photo yet
N 440 YD 3.7 MI · LOOP
DOGS WELCOME

Stokesley Packhorse Bridge and the River Leven

Stokesley
No reviews yet
3.7MILES
1:30TIME
10mCLIMB
75%OFF-ROAD
Off-lead allowed Livestock — leads on

A flat 3.7-mile riverside stroll with barely 10 metres of ascent, an hour and a half, on mown grass paths and field edges beside the River Leven, finishing over the seventeenth-century packhorse bridge in the town. Start from Stokesley market place, which has free short-stay parking and frequent buses from Middlesbrough and Great Ayton. The Leven is shallow and easy to get in and out of the whole way, there are bins and benches along the town stretch, and dogs can be off the lead on the riverside greens, though the outer field section is sometimes grazed.

VERIFIED 29 JUL 2026 VIEW WALK ›
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1 MILE © OpenStreetMap contributors 8 MI · LOOP
SOME LIMITS

Stokesley to Great Ayton Field Paths

Stokesley · TS9 5DL
No reviews yet
8MILES
3:15TIME
20mCLIMB
85%OFF-ROAD
Livestock — leads on

Eight flat miles with barely 20 metres of ascent and around three and a quarter hours, tracking the River Leven across the vale between the two towns and returning on the paths north of the river; there is no climbing at all but the arable headlands are heavy going in winter and there are numerous stiles and kissing gates. It starts in Stokesley town square, where parking is free for three hours and the Arriva 81 runs to Great Ayton if you would rather walk one way and ride back. The Leven is within reach for most of the route and gives easy drinking and a shallow paddle, but almost every field on this walk is farmed, with sheep and cattle in the pastures and standing crops in the arable, so this is a lead walk with only short releases.

VERIFIED 29 JUL 2026 VIEW WALK ›
WAGFINDER No photo yet
1 MILE © OpenStreetMap contributors 14.6 MI · LOOP
SOME LIMITS

Stokesley to Roseberry Topping Long Round

Stokesley · TS9 5DL
No reviews yet
14.6MILES
6:34TIME
440mCLIMB
85%OFF-ROAD
Off-lead allowed Livestock — leads on

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.

VERIFIED 29 JUL 2026 VIEW WALK ›

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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
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