Walk the wailing Wain Stones

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Lowland and Hill Walks
Sat 22 Aug
2026

11 people attending

9 places left

Your price
£12.50
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11+ miles, several steep ascents and descents.

Total distance: about 18 km (approx. 11.2 miles), with 710 m (2325 feet) of ascent. Approximately 6 hours, including lunch. This walk includes some steep climbs and descents, as well as relatively flat sections (moorland). There is little shade for most of the walk, and given the elevation, it is usually windy. 

Starting from the Clay Bank, we ascend towards the coast-to-coast path. This initial section takes us up above Hasty Bank (398 m) with magnificent views North, towards Middlesbrough and beyond. We then walk along a relatively flat stone path to the Wainstones. 

The name "Wainstones" (a prominent sandstone outcrop on Hasty Bank in the North York Moors) is believed to originate from the ancient Anglo-Saxon word wanian, meaning to lament or grieve. Historically, the stones were called the "Stones of Lamentation", and legend suggests they may have been a burial site for a slain Danish chieftain. Another theory is that the jumbled, rock-strewn gap was simply viewed as a place to mourn or perform rituals. Alternatively, the name is sometimes linked to the archaic word "wain" (a poetic term for a wagon or cart), as the rocks' shape can vaguely resemble an old carriage from certain angles.

After a descent, and a short valley section, we are soon climbing again, this time towards Cold Moor (401 m). Despite the name, it was warm when I visited ;)

Continuing on, we climb above Carlton Bank to reach Cringle Moor before heading on to the Lord Stones.

 The "Lord Stones" refer to a prominent collection of ancient boundary markers and prehistoric stones. The name originates from the Three Lords' Stone, which historically marked the point where the estates of three local lords met. Bronze Age Barrow: The primary stone sits atop the perimeter of an ancient Bronze Age burial mound. This area formed a small cemetery and ceremonial site thousands of years before the local estates were formed

We then reach Lordstones cafe, where refreshments can be bought. There are benches and a large flat area nearby, for those who bring a packed lunch.

After another more gradual ascent, we cross an exposed section of moorland. Our gradual descent takes us through a short section under trees. We then resume a gradual ascent towards Urra Moor. This section passes through an area where many partridges breed, so any dogs need to be kept under close control. We return to the path we started along earlier in the day, for a final 1.5 miles or so back to the car park. 

For those who may like a drink after, the best local option is The Dudley Arms at Ingelby Greenhow, less than 3 miles away.

Dogs: Well-behaved, under control dogs are welcome at this event.

Dogs should be kept on a lead whenever signposted, whenever we are in the vicinity of livestock, and at the event leader's request. Many stretches of this walk include sheep roaming. I would also note that there are a few up-and-over wall stiles towards the end of the walk, so you get a bit of an upper-body workout lifting your dogs over them. You'll need to make sure you're carrying sufficient extra water for your four-legged friend. We do not encounter much natural water on this walk. If you're unsure, contact the leader for guidance.

If the event is fully booked: Please join the waiting list as people frequently drop out during the week before an event, and you are likely to get a place on the walk. 

If this is your first OutdoorLads walk event, we’ll make sure you feel welcome. Please check out the My First Event page, and don’t hesitate to drop me a message if you have questions or want to know more about this walk.

Image/photo credits:  All leader's own images - with permission for OutdoorLads to use.