Helmsley Castle & Rievaulx Abbey Loop
Time: 4 hrs 54 mins Distance: 11 miles / 17.7 km Average pace: 2.2 mph / 3.6 km/h Uphill: 975 ft / 300 m Downhill: 1000 ft / 300 m
This beautiful walk begins and ends in the historic market town of Helmsley, winding gently through ancient woodland, open fields and riverside paths. From the heart of the town, the route passes Helmsley Castle, opening out to views across the Rye Valley before heading west along well-trodden countryside tracks and footpaths.
The trail drops through woodland and pasture to reach the peaceful ruins of Rievaulx Abbey — one of Yorkshire’s most atmospheric historic sites, set beside the River Rye. Take time to pause here, enjoy the quiet of the valley and, in season, carpets of wildflowers and bluebells before beginning the return.
This loop is a balanced blend of history, nature and classic North Yorkshire scenery, with gentle climbs, expansive views and a strong sense of place. It pairs naturally with a visit to The Feather Trail, either before setting out or on your return.
On the Trail
This longer loop gradually draws you out of Helmsley and into the quieter folds of the Rye Valley. It’s a walk that unfolds slowly, rewarding patience with shifting views, layered history and a real sense of distance travelled.
Leaving the town, the route climbs steadily through woodland and open farmland. The ascent is gentle rather than demanding, offering time to look back towards Helmsley and out across the surrounding countryside. Underfoot, paths vary between firm tracks and softer ground, particularly after wet weather.
Further west, the landscape becomes more enclosed and peaceful as the trail leads down towards the River Rye. The approach to Rievaulx Abbey is a quiet highlight — the ruins revealing themselves slowly, framed by trees and water. It’s a natural place to pause, take stock and absorb the stillness before turning back.
The return journey climbs again, offering a different perspective over the valley and surrounding hills, before easing gradually back towards Helmsley. With nearly five hours on the trail, this walk feels like a full day out — unhurried, purposeful and shaped by the rhythm of the land.
Best walked at a steady pace, this is a route for those who value time outdoors, varied terrain and journeys that allow space to think. A walk that carries you away from the everyday, then gently returns you, without hurry.
