4.7
(39)
1,994
riders
171
rides
Road cycling around Pockley offers access to the diverse landscapes of the North York Moors National Park. The region is characterized by elevated rolling moorland, deeply incised dales, and quiet country roads. To the south, the Howardian Hills and Vale of Pickering provide varied terrain, from rolling hills to flatter, pastoral routes. This area presents a network of roads suitable for road cyclists seeking both challenging ascents and scenic, less strenuous rides.
Last updated: July 22, 2026
11
riders
93.2km
04:36
1,180m
1,180m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
5
riders
93.4km
04:45
1,490m
1,490m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

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4
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(3)
61
riders
55.2km
02:35
690m
690m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(1)
25
riders
64.8km
03:16
1,030m
1,030m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
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Each of the sacred monuments that you repeatedly encounter – despite all the differences in their external design – has a common concern: The cross that rises here not only wants to attract the viewer's gaze, but – and this is primarily – to make him think of God. Not only in theological books, but even in secular literature, God's voice is often represented, and this is even often the case in crime novels. For example, Ellis Peters set the series of novels about the Benedictine 'Brother Cadfael', which is set in 12th-century England, in the surroundings of a monastery. In "The Virgin in the Ice" it says: "And yet life, clinging to faith, the tenacious struggle with fate had to go on, the land had to be cultivated year in, year out. Plough and harrow must not rest, and one had to take care of sowing and harvesting the fruits of the earth as much as here, in the monastery and church, of sowing and harvesting souls." I wish the viewer here in front of the cross a good thought for his soul.
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A punchy climb out of Bransdale up Cowhouse Bank before the long roll down into Helmsley.
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One of the most iconic loops in the North York Moors - the Bransdale loop to Cockayne is a cycling paradise.
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Wayside crosses are one of several types of Christian cross erected during the medieval period, mostly from the 9th to 15th centuries AD. In addition to serving the function of reiterating and reinforcing the Christian faith amongst those who passed the cross and of reassuring the traveller, wayside crosses often fulfilled a role as waymarkers, especially in difficult and otherwise unmarked terrain. The crosses might be on regularly used routes linking ordinary settlements or on routes having a more specifically religious function, including those providing access to religious sites for parishioners and funeral processions, or marking long-distance routes frequented on pilgrimages. Over 350 wayside crosses are known nationally, concentrated in south west England throughout Cornwall and on Dartmoor where they form the commonest type of stone cross. A small group also occurs on the North York Moors. The wayside cross and boundary marker known as Young Ralph survive complete even though previously broken and repaired. The cross marks the highest point on the old road from Keldholme in the south of the moors to Castleton in the north. It also marks the boundary of the Wapentake of Pickering Lyth. It has been adopted as the symbol of the North York Moors National Park and has been a listed monument since 1938.
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This is where to turn off the Bransdale road to ascend to meet Rudland Rigg.
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Beautiful spot. It's a sharp U over the bridge so don't try and carry any speed into the immediate next ascent.
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Road cycling around Pockley offers a diverse range of experiences, primarily within the North York Moors National Park. You'll find routes traversing elevated rolling moorland, deeply incised dales like Ryedale and Farndale, and quiet country roads. To the south, the Howardian Hills provide rolling terrain, while the Vale of Pickering offers flatter, more pastoral rides. The region caters to various abilities, from challenging climbs to scenic, less strenuous options.
There are over 180 road cycling routes available around Pockley on komoot. These routes range in difficulty, with approximately 40 easy, 120 moderate, and 20 difficult options, ensuring there's something for every cyclist.
Yes, the North York Moors are renowned for their challenging ascents. Notable climbs in the wider region include Rosedale Chimney, known for its gradients up to 30%, as well as Sutton Bank and White Horse Bank. These offer a significant test for experienced road cyclists.
For longer rides, you could consider routes like the North York Moors National Park loop from Helmsley, which covers nearly 60 miles and explores expansive moorland and valleys. Another option is the Helmsley loop to Rievaulx Abbey & the Cleveland Hills, a similar distance featuring significant climbs and historical sights.
While the North York Moors can be challenging, the region also offers easier-going experiences. The Vale of Pickering, to the south of the Moors, provides flat, quiet lanes through a pastoral landscape, suitable for a more relaxed ride. There are approximately 40 easy road cycling routes available on komoot in the Pockley area.
The area boasts stunning natural beauty. You'll encounter heather-clad moorland offering panoramic views, deep valleys (dales), and ancient woodlands. Highlights include Urra Moor – Highest Point of the North York Moors, and the dramatic rock formations of The Wainstones. The North York Moors National Park extends to a rugged coastline further east, offering sea views on longer routes.
Yes, several routes pass by or near historical sites. For instance, the Helmsley loop to Rievaulx Abbey & the Cleveland Hills passes by the historic Rievaulx Abbey. You might also encounter sites like the Bank Top Iron Kilns or picturesque villages such as Hutton-le-Hole, which offer opportunities for refreshment and exploration.
The road cycling routes around Pockley are highly regarded by the komoot community, holding an average rating of 4.7 stars from over 40 reviews. Cyclists often praise the varied terrain, from challenging moorland climbs to serene country roads, and the stunning natural beauty of the North York Moors National Park.
Yes, the region is home to established cycling networks. The North York Moors Cycleway is a 171-mile figure-of-eight loop that guides cyclists along quieter roads, showcasing the landscape's highlights, including high moorland, valleys, and coastal sections. The Moor to Sea Cycle Network also offers 150 miles of pedal-powered freedom through diverse scenery.
Many road cycling routes in the Pockley area pass through charming North Yorkshire villages and market towns. These often provide excellent opportunities to stop for refreshments at local tea rooms, cafes, and traditional pubs, allowing you to refuel and experience local hospitality.
The best time for road cycling around Pockley is generally from spring through autumn. During these seasons, the weather is typically milder, and the heather on the moors is in bloom in late summer, offering spectacular views. However, be prepared for changeable weather conditions, as is common in North Yorkshire.
Yes, many of the road cycling routes around Pockley are designed as circular or loop trails, allowing you to start and finish in the same location. For example, the Blakey Bank Summit – Hutton-le-Hole village loop from Nawton is a popular circular option, as is the Ousegill Bridge – Hutton-le-Hole village loop from Helmsley.


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