Best mountain peaks around Stokesley are found in a region characterized by the dramatic landscapes of the North York Moors National Park and the Cleveland Hills. Stokesley, a market town in North Yorkshire, serves as a gateway to these notable peaks and significant hills. The area offers a variety of experiences for walkers and nature enthusiasts, with hills rising abruptly from the flat Tees Valley. Part of the Cleveland Way National Trail also runs along these hills, enhancing their accessibility.
…Last updated: May 6, 2026
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Until 1912, Roseberry Topping had a smooth, sugarloaf‑like peak. A geological fault combined with underground mining caused a massive collapse, giving the summit its modern jagged profile. The climb up from the car park is steep and can be very busy, even before sunrise in winter where you can see a small procession of torches slowly ascending.
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This is where I realised wearing new boots for a hike this long was a BAD idea!
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Lots of view points, people rock climbing and the up and downs test you as they are short, but a touch punchy for their short elevation!
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Just off the Cleveland Way and about halfway between Carr Ridge to the west and Bloworth Crossing to the east, spectacular views all around on a clear day.
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Urra Moor is fairly large and criss-crossed with several walking routes, some more popular than others. As a result, there are great panoramic views to be had in all directions. https://en.wikipedia.org/wiki/Urra_Moor
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Judging from the number of recommendations, photos and tips, this is a hugely popular spot. If you can, get up there nice and early (I started 5.30am in May) to catch the rising sun and see the stones in a mix of sunlight and shadow, both from afar and close up. Spectacular rock formations and views all round.
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More spectacular views. The approach from the west is easier with a more gentle incline than the approach from the east, which involves a series of twisting turning steep steps, good safe footing but hard going both up and down.
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The region around Stokesley, particularly within the North York Moors National Park and the Cleveland Hills, features several notable peaks. Among the most distinctive are Roseberry Topping Summit, known as the 'Yorkshire Matterhorn' for its unique pyramid shape, and The Wainstones, a fierce-looking rocky outcrop on Hasty Banks. Other significant points include Carlton Bank Summit Trig Point with its panoramic views, and Urra Moor, which is the highest point of the North York Moors.
The peaks and hills around Stokesley offer spectacular and varied views. From Roseberry Topping, you can see the North York Moors and beyond. Carlton Bank provides extensive views of Teesside, the undulating North York Moors, and on clear days, even the Pennines. From The Wainstones, you can admire the Cleveland Hills to the south and the plains leading to Middlesbrough to the north. Urra Moor offers vast panoramic views in all directions across the moorland.
Yes, the Cleveland Hills offer several challenging hiking opportunities. The ascent to Roseberry Topping Summit is considered relatively challenging but manageable, with various route options of differing difficulties. Trails around The Wainstones and Carlton Bank, especially from the east, can involve steep sections and offer a good workout. The Cleveland Way National Trail, which runs along these hills, also includes sections with elevation gain and demanding terrain.
The region is rich in history. Urra Moor, the highest point of the North York Moors, is known for its prehistoric remains, including burial mounds and carved stones with cup and ring carvings. Similarly, on the lower ground surrounding The Wainstones, there are collections of rocks with prehistoric carvings, though these can be difficult to discern due to erosion.
Beyond hiking and climbing the peaks themselves, the area around Stokesley offers a variety of outdoor activities. You can find numerous running trails, such as the challenging Roseberry Topping Summit – The Wainstones loop. Cycling is also popular, with routes like the Great Ayrton, Commondale & Gisborough loop for touring bicycles, and various road cycling routes. Many trails are part of the Cleveland Way National Trail, offering extensive walking opportunities.
While some peaks offer challenging ascents, there are also more manageable sections and routes suitable for families. For instance, while the summit of Roseberry Topping can be challenging, there are varying difficulty levels for its paths. The broader North York Moors National Park offers many trails that cater to different fitness levels, including easier walks around the base of some hills or along less steep sections of the Cleveland Way.
Public transport options exist to access parts of the North York Moors National Park and its trails from Stokesley. While direct routes to every trailhead might be limited, services often connect Stokesley to nearby towns like Great Ayton, which can serve as a starting point for walks towards Roseberry Topping. It's advisable to check local bus schedules for the most current information on routes to specific trailheads.
Parking is available near Roseberry Topping, often managed by organizations like the National Trust. Specific car parks are located at the base of the peak, providing access to various trailheads. It's recommended to arrive early, especially on weekends or during peak season, as these popular spots can fill up quickly.
The best time to hike the peaks near Stokesley, within the North York Moors, is generally from spring through autumn (April to October). During these months, the weather is typically milder, and the moorland is vibrant with heather in late summer. Winter walks are possible but require appropriate gear due to potentially harsh conditions, including cold temperatures, strong winds, and occasional snow on the exposed moorland.
Yes, there are options for refreshments near the hiking areas. Great Ayton, a village close to Roseberry Topping, has cafes and pubs popular with hikers. Near Clay Bank, which is close to Carlton Bank, you can find cafes and pubs. These establishments provide a welcome stop before or after exploring the trails.
Visitors highly appreciate the mountain peaks around Stokesley for their dramatic landscapes, spectacular views, and the sense of peace offered by the expansive moorland. The unique shapes of peaks like Roseberry Topping and the distinctive rock formations of The Wainstones are particularly popular. The komoot community has shared 229 photos and given 381 upvotes, highlighting the visual appeal and enjoyable experiences these locations provide.
Many hiking trails in the North York Moors National Park, including those around peaks like Roseberry Topping, are dog-friendly. However, it's crucial to keep dogs on a lead, especially during lambing season (spring) and ground-nesting bird season (spring/summer), or when livestock are present. Always follow local signage and the Countryside Code to ensure a safe and enjoyable experience for everyone.


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