4.7
(30)
2,655
runners
14
runs
Jogging around Stokesley offers diverse landscapes, from the flat paths alongside the River Leven to the challenging ascents of prominent hills. The region is characterized by its proximity to the North York Moors National Park, featuring moorland, distinctive rocky outcrops like The Wainstones, and scenic river valleys. These natural features provide varied terrain for running, catering to different fitness levels.
Last updated: June 21, 2026
50
runners
46.0km
05:28
1,140m
1,140m
Hard run. Very good fitness required. Sure-footedness, sturdy shoes and alpine experience required.
26
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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9
runners
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
8
runners
23.7km
02:30
110m
110m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
Moderate run. Good fitness required. Mostly paved surfaces. 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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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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Walking boots is a must as the terrain is very uneven and can get slippy if it’s been raining
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Komoot offers over 15 running routes around Stokesley, catering to various preferences and fitness levels. These include everything from easy riverside paths to challenging moorland ascents.
Yes, Stokesley has several easy running routes perfect for beginners or those looking for a relaxed jog. These often feature relatively flat paths, such as those along the River Leven. An example is the shorter loops around Stokesley Packhorse Bridge.
The terrain around Stokesley is quite varied. You'll find relatively flat, picturesque paths along the River Leven, as well as more challenging moorland trails with significant elevation changes, especially as you venture towards the North York Moors National Park. Surfaces can range from paved paths to natural dirt trails.
Absolutely. For a challenging run with significant elevation gain and panoramic views, consider routes that incorporate prominent landmarks like Roseberry Topping and The Wainstones. The Roseberry Topping Summit – The Wainstones loop from Stokesley is a difficult 28.7-mile trail with over 1100 meters of ascent.
Many running routes in Stokesley offer stunning scenery and pass by notable landmarks. You can enjoy views of the picturesque River Leven, the historic Stokesley Packhorse Bridge, and the distinctive Roseberry Topping Summit. Other features include the dramatic The Wainstones and the expansive moorland of the North York Moors.
Yes, many of the easier, flatter routes, particularly those along the River Leven or shorter loops within Stokesley, are suitable for families. These paths often provide a pleasant and safe environment for a family jog or walk.
The Stokesley area is generally very dog-friendly, with many trails suitable for running with your canine companion. Routes like 'Bonnys Walk' and various riverside paths are popular choices. Always remember to keep dogs under control, especially near livestock, and follow local guidelines.
The summer months are generally ideal for running in Stokesley, offering warmer weather and longer daylight hours. However, spring and autumn also provide beautiful scenery with fewer crowds, though the weather can be less predictable. Winter runs can be invigorating, but trails may be muddy or icy, especially on higher ground.
Yes, many of the running routes around Stokesley are circular, allowing you to start and finish in the same location. Examples include the Stokesley Town Centre – Stokesley Packhorse Bridge loop and the Great Ayton Village Centre – Stokesley Packhorse Bridge loop.
The River Leven is a prominent feature in Stokesley, and several running routes follow its picturesque banks. These paths offer relatively flat terrain and scenic views, making them popular for a relaxed jog. A route from Stokesley to Great Ayton, approximately 2.5 miles, is a great option along the river.
For those seeking longer distances, Stokesley provides excellent options. The Roseberry Topping Summit – The Wainstones loop from Stokesley is a substantial 28.7-mile trail, offering a full day's adventure for experienced long-distance runners.
The running trails in Stokesley are highly rated by the komoot community, with an average score of 4.5 stars from over 30 reviews. Runners often praise the diverse landscapes, from tranquil riverside paths to challenging moorland climbs, and the stunning views from landmarks like Roseberry Topping.
Yes, parking is generally available in and around Stokesley, often near the town center or at designated car parks close to popular trail access points. It's advisable to check specific route details for the most convenient parking locations.
Stokesley and its surrounding villages offer various pubs and cafes, many of which are conveniently located near popular running routes. You can easily plan your run to include a refreshing stop for a drink or a bite to eat, especially in the town center or Great Ayton.


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