4.5
(1148)
7,946
hikers
268
hikes
Hikes around Oswaldkirk explore the landscape where the North York Moors National Park meets the Howardian Hills. The region is characterized by rolling hills, extensive woodlands, and gentle streams like the Holbeck and White Beck. The village's position at the foot of a wooded escarpment provides access to trails with long-distance views over the surrounding countryside.
Last updated: May 12, 2026
4.7
(3)
6
hikers
11.2km
03:13
270m
270m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5
hikers
10.9km
03:00
190m
190m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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4.2
(5)
9
hikers
11.0km
02:56
110m
110m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5.0
(1)
12
hikers
8.03km
02:09
100m
100m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
5
hikers
14.4km
04:00
260m
260m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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Save some energy for the long final stretch - not the steepest part but energy sapping.
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Very nice spot. If you are headed east up Drakendale Gill, then the woodland path is quite steep, but then flattens out a bit and becomes more of a plantation track as you proceed through The Royalty and College Moor.
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Ampleforth Abbey has been a working abbey for Benedictine monks since 1802. It's an imposing and imposing space. The Abbey Church can be visited, and there is also a tearoom here and Visitor Centre. The impressive grounds around the Abbey include the Ampleforth College, which is an independent Catholic boarding school.
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This is quite a gem. In this tiny village, there is a miniature railway where, on certain Sundays, you can ride on the little trains between Easter and autumn. Great fun for both children and adults alike! The village hall building (used to be a train station) serves teas and coffees when the rides are open, and there is a lovely playground outside too.
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This is one fabulous place to be: a very picturesque and beautiful little lake, with little piers on its banks in a few places. The tracks and paths around it are well-managed (thus easy to run on). On a sunny day, the waters get amazingly blue colours and the scene is truly Impressionistic!
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This is a lovely little lake in Yearsley Woods to jog your way up to. Note, all the maps I've seen show two ponds here - however, only this one remains in reality; the other one has been drained since and is essentially a marshland now.
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Yes, the area is well-suited for circular hikes. Many trails are designed as loops, allowing you to start and end in the same place without retracing your steps. These routes explore the varied landscape of the Howardian Hills and the edge of the North York Moors, often combining woodland paths with open countryside.
For a shorter, manageable walk that's great for families, consider the Lower Fish Pond loop from Gilling. It's an easier route with relatively little elevation gain, making it suitable for a wide range of ages and abilities while still offering lovely scenery.
Most footpaths and trails around Oswaldkirk are dog-friendly, but it's important to be mindful of the landscape. You'll be walking through farmland with livestock and areas with ground-nesting birds, especially in the North York Moors National Park. Always keep your dog under close control, and on a lead where required by signage.
The region's position at the foot of a wooded escarpment means many trails offer excellent long-distance views. Hikes that climb towards Beacon Bank are particularly rewarding, providing panoramic vistas over the Coxwold-Gilling Gap and towards the Howardian Hills National Landscape, a highly-regarded area known for its rolling, forested scenery.
Absolutely. A popular choice for history enthusiasts is the Byland Abbey Ruins – The Hub Café, Ampleforth loop from Ampleforth. This moderate hike features the impressive, free-to-visit ruins of a former medieval monastery, offering a fantastic combination of history and nature.
There's a good mix of difficulties. You'll find over 250 routes in total, with the majority being rated as moderate. These typically involve some elevation and varied terrain. There are also nearly 100 easy trails perfect for gentle strolls, as well as more challenging options for experienced hikers looking to tackle the steeper sections of the moors.
Both are excellent choices. Oswaldkirk offers a quieter, village-based experience right at the confluence of the Howardian Hills and the North York Moors. Helmsley is a larger, bustling market town that also serves as a major hub for walkers, offering more amenities. Your choice depends on whether you prefer a tranquil village setting or the convenience of a larger town.
The trails in this area are highly rated by the komoot community, with thousands of hikers having explored the region. Reviewers often praise the beautiful long-distance views, the mix of peaceful woodland and open farmland, and the well-maintained network of footpaths.
Yes, the area is rich in woodland. Many local routes pass through Oswaldkirk Hagg Wood. For a dedicated forest experience, the nearby Yearsley Woods is a popular favorite among locals, offering a network of trails through a large forested area. Similarly, the North Riding Forest Park provides extensive trails for both hiking and cycling.
Parking availability depends on your chosen route's starting point. For walks beginning in villages like Oswaldkirk, Ampleforth, or Gilling, on-street parking is often available, but please park considerately. Some popular trailheads, like those near Sproxton, have informal roadside parking areas. It's always best to check your specific route details for parking suggestions.
While the immediate Oswaldkirk area is known more for its gentle streams and rolling hills, a short drive will take you to some of the North York Moors' famous waterfalls. Mallyan Spout Waterfall near Goathland is a highly-rated natural attraction, though the walk to it can be a bit of a scramble over rocks.


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