4.5
(1496)
14,275
hikers
408
hikes
Hiking around Stokesley offers access to diverse landscapes on the edge of the North York Moors National Park. The region features vast expanses of heather moorland, woodlands, and distinctive hills like Roseberry Topping. Gentler routes follow the picturesque River Leven and wind through rolling pastures, providing varied terrain for outdoor exploration.
Last updated: April 26, 2026
4.3
(6)
56
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
1.0
(1)
36
hikers
5.08km
01:17
10m
10m
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.

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15
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.3
(3)
9
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.0
(1)
7
hikers
23.5km
06:34
440m
440m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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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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Great views of the eastern flank of Roseberry Topping from the track leading to Little Roseberry.
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Gribdale Gate is a small, free, 24‑hour Forestry England car park on Dikes Lane near Great Ayton, offering around 40 spaces and direct access to Roseberry Topping, Captain Cook’s Monument, and Coate Moor
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Great views and early on a Sunday morning is best to beat the crowds. The obelisk is hollow and originally had a doorway you could walk through, before it was sealed during a 19th‑century restoration. A lightning strike in 1960 almost split the monument down the middle after the lightning conductor installed in 1895 rusted away. Earlier lightning strikes in the 19th century had already blown off the original doorway and obliterated the cast‑iron plaques. Fun fact - allegedly - the monument contains a hidden time capsule. When the foundation stone was laid in 1827, commemorative items were placed inside, including a portrait of Captain Cook and a glass plate etched with details of the event.
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Directly in front of the monument, take a stroll about 30-50 paces and you will have some very decent views of the area!
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Walking boots is a must as the terrain is very uneven and can get slippy if it’s been raining
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mostly cobble stoney surface..be careful with footing
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Stokesley offers a wide variety of hiking experiences, with over 400 routes available. These range from gentle riverside strolls to more challenging moorland ascents, catering to all levels of hikers.
The terrain around Stokesley is incredibly diverse. You'll find vast expanses of heather moorland, particularly within the North York Moors National Park, alongside picturesque river walks along the River Leven and paths winding through rolling pastures. Distinctive hills like Roseberry Topping also provide elevated viewpoints and more rugged sections.
Yes, Stokesley has many easy trails perfect for families. Over 180 routes are classified as easy. A great option is the Stokesley Packhorse Bridge – Stokesley Castle Hill loop from Stokesley, which is a gentle 4.5 km walk through historical sites and the countryside.
Many trails around Stokesley are dog-friendly, especially those on public footpaths and bridleways. However, as much of the area borders or is within the North York Moors National Park, it's important to keep dogs on a lead, particularly during lambing season or when livestock are present, and to protect ground-nesting birds on the moorland. Always check local signage.
Yes, the majority of hiking routes around Stokesley are circular, allowing you to start and finish in the same location. For example, the Waterfall Park, Great Ayton – Great Ayton Village Centre loop from Stokesley is a moderate circular path exploring scenic parkland and village surroundings.
Hiking near Stokesley offers access to several iconic natural landmarks and stunning viewpoints. You can ascend to the Roseberry Topping Summit for panoramic views, explore the distinctive The Wainstones, or visit the Carlton Bank Summit Trig Point for breathtaking vistas across the moors. The Round Hill Summit (Highest Point of Urra Moor) also offers spectacular views.
Absolutely. For experienced hikers seeking a challenge, the Roseberry Topping Summit – View of Roseberry Topping loop from Stokesley is a popular choice. This difficult 23.5 km route involves a significant ascent to the iconic Roseberry Topping, rewarding you with extensive views. There are 29 difficult routes in total.
Stokesley itself is known for its friendly atmosphere and independent shops, cafes, and pubs, making it easy to combine a walk with refreshments. You can find routes like the G and Tea Café loop from Stokesley, which is an easy 5 km walk designed to incorporate a local cafe stop.
The best time to hike in Stokesley largely depends on your preference. Spring and summer offer vibrant wildflowers and heather, with longer daylight hours. Autumn brings stunning colours to the moorland and woodlands. While winter can be beautiful, some higher moorland routes may be more challenging due to weather conditions. Always check local forecasts before heading out.
Yes, you can find walks that include scenic water features. The area around Great Ayton, close to Stokesley, features Waterfall Park. A good option is the Great Ayton Village Centre – Waterfall Park, Great Ayton loop from Stokesley, which allows you to explore this picturesque area.
The hiking trails around Stokesley are highly regarded by the komoot community, with an impressive average rating of 4.5 stars from over 1400 reviews. Hikers often praise the diverse landscapes, from the dramatic moorland to the tranquil river paths, and the rewarding views from prominent landmarks like Roseberry Topping.


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