Helmsley is one of those places that gets under your skin, in a good way. The market town of Helmsley sits right on the edge of the North York Moors National Park, and whether you’re after a gentle walk along a riverbank or something more ambitious through ancient woodland and past medieval ruins, the walking here is some of the best in North Yorkshire. Here are the walks worth knowing about.
1. The Helmsley Circular Walk
The classic. The Helmsley circular walk takes you out of Helmsley Market Square and into the surrounding countryside, looping back through a mix of riverside paths, farm tracks and woodland. It’s a varied walk that gives you a proper taste of the landscape around the town without needing a car to get anywhere. Pick up the route from the Cleveland Way car park and follow the footpath signs — the route is well marked and manageable for most skill levels. You’ll get lovely views back over the town and Helmsley Castle along the way.
Distance: Around 3-4 miles depending on the route variation you take Good for: First-time visitors, families, dog walkers
2. Helmsley to Rievaulx Abbey
This is the walk that most people come to Helmsley for, and it earns every bit of its reputation. From Helmsley, the route follows the River Rye through Ryedale, passing through peaceful woodland and open countryside before dropping down into the wooded valley where historic Rievaulx Abbey sits. The abbey itself is managed by English Heritage and is a breathtaking medieval ruin — one of the finest in the country. The return route takes you back along Rievaulx Bank with fine views across the valley, or you can loop back via Rievaulx Bridge for a slightly different return.
It’s a lovely circular walk of around 7 miles, but shorter variations exist if you want to keep it to a more gentle walk. History lovers and nature seekers will both get plenty out of this one.
Distance: Around 7 miles circular, shorter options available Good for: History lovers, confident walkers, dog walkers
3. Duncombe Park
Just outside Helmsley, Duncombe Park is a national nature reserve and one of the most underrated walking spots in North Yorkshire. The parkland sits within a conservation area and is home to some of the oldest and largest trees in England, as well as rare insects that depend on the ancient woodland habitat. The riverside paths through the park follow the River Rye through tranquil settings, and the formal terraces above give wonderful views across Ryedale.
It’s a lovely walk that doesn’t require a huge amount of effort — perfect if you want beautiful countryside views without committing to a full day out. The walled garden at Duncombe Park is also worth a look if it’s open.
Distance: Variable — 2 to 5 miles depending on route Good for: Nature seekers, families, anyone wanting a gentler walk
4. Beck Dale and Ash Dale
For something a little different, Beck Dale and Ash Dale offer a quieter, more tucked-away walking experience. These wooded dales sit just outside Helmsley and are part of the wider network of public footpaths that criss-cross the North York Moors. Borough Beck runs through the bottom of the valley, and in spring the wildflower meadows along the route are genuinely lovely. It’s a peaceful, unhurried walk that rewards those who take it slowly — the kind of local walk that feels like a proper find.
The route involves a short section along a minor road before picking up the public path again, so keep an eye out for footpath signs.
Distance: Around 3-4 miles Good for: Nature seekers, dog walkers, anyone after a quieter route
5. The Cleveland Way from Helmsley
Helmsley is actually the official start point of the Cleveland Way, one of England’s great long distance walking routes. You don’t have to walk the whole thing — even a short section out of town gives you a proper taste of the North York Moors, with open countryside, great views and that sense of space that the moors do better than almost anywhere. The Cleveland Way heads north from Helmsley Market Place towards Cold Kirby and beyond, and even a few miles out and back makes for a scenic walk with some of the best countryside views in the area.
If you’ve walked any section of the Cleveland Way near Whitby, you’ll recognise the landscape — it’s that same open, dramatic moorland.
Distance: As long or short as you like — even 2-3 miles out and back is a good introduction Good for: All walkers, those wanting to dip into a longer route without committing to it
Before You Go
Helmsley itself is well worth time before or after your walk. The market place has independent shops, good cafes and Helmsley Castle right on its doorstep — also managed by English Heritage and well worth a visit if you haven’t been. For places to eat, places to stay and more things to do in and around the town, I’ve got a full set of Helmsley guides:
- Best things to do in Helmsley
- Places to eat in Helmsley
- Best places to stay in Helmsley
- The best photography walks in Helmsley
And if you’re planning more walking in the region, my Yorkshire Wolds walks post and best autumn walks in Yorkshire are both worth a read.