Cholesbury-Cum-St Leonards
Cholesbury-Cum-St Leonards
4.6
(143)
11,484
runners
691
runs
Jogging routes around Cholesbury-Cum-St Leonards traverse the diverse landscapes of the Chiltern Hills, an Area of Outstanding Natural Beauty. The region features rolling hills, ancient woodlands, and open meadows, providing varied terrain for runners. Chalk grasslands and scenic valleys also contribute to the area's natural composition. This environment offers a range of physical features suitable for different running preferences.
Last updated: May 26, 2026
5.0
(1)
21
runners
7.52km
00:47
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
3.0
(1)
11
runners
6.87km
00:43
60m
50m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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10
runners
5.00km
00:38
110m
110m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
9
runners
11.2km
01:11
110m
110m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
7
runners
6.02km
00:38
30m
30m
Moderate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Cholesbury-Cum-St Leonards
Stiftung Lesen review: A little mouse is walking around in the forest and enjoying life. And then she meets a fox, an owl and a snake, all of whom invite her to their homes very warmly and certainly without any ulterior motives. Fortunately, the little mouse is not stupid. And so she politely but firmly declines the invitations - because she already has a date: with the Gruffalo! He has terrible claws, teeth, tusks and paws and loves to eat fox skewers, snake puree or owls with icing. No wonder that the would-be hosts make a hasty getaway. And the mouse is having a great time, because she just invented the Gruffalo! Or maybe not?? A wonderfully rhymed read-aloud at its finest, which with lots of imagination, wit and hidden meaning will delight not only children from around 5 years of age.
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Interesting place of ancient fort. You can see barriers from soil and imagine how high they were 7000 years ago.
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The striking clock tower in the centre of Chesham looks older, but it's not: it was built in 1992! However, it's the tower that's new, not the clock itself, which used to be a part of Chesham Town Hall.
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You can sometimes even spot wildlife here.
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The hill (260m) is in the middle of the Wendover Woods. It'd be difficult to tell unless you know, but there is an Iron Age hill fort here, which would've been a very strong position in the past. Once you know, it's possible to find the fort's remains amongst the trees. There is an information board here, providing further information about the site.
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It's a lovely pub here in Botley Road for some food and drink. Be sure to go around the back - in the summer, you should be able to witness a lovely wildflower meadow on the grass here!
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This is a lovely, family run cafe that serves gorgeous hot beverages and delicious food. It enjoys marvellous views across the Chiltern countryside. There are plenty of activities to enjoy nearby, from hiking and cycling to a Go Ape course up in the trees.
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There are over 670 running routes around Cholesbury-Cum-St Leonards, offering a wide variety of options for different preferences and fitness levels. These include 54 easy routes, 499 moderate routes, and 122 difficult routes.
The running trails in Cholesbury-Cum-St Leonards traverse diverse landscapes within the Chiltern Hills. You can expect to encounter rolling hills, ancient woodlands (like Captains Wood and Wendover Woods), open meadows, and distinctive chalk grasslands. This varied terrain provides both challenging inclines and rewarding scenic views.
The running routes in Cholesbury-Cum-St Leonards are highly rated by the komoot community, with an average score of 4.6 stars from over 120 reviews. Runners often praise the area's diverse landscapes, from ancient woodlands to open chalk grasslands, and the well-established network of paths that cater to various fitness levels.
Yes, Cholesbury-Cum-St Leonards offers 54 easy running routes, perfect for beginners or those looking for a more relaxed run. These paths typically have minimal elevation gain and cover shorter distances, allowing for a comfortable and enjoyable experience.
Absolutely. For experienced runners seeking a challenge, there are 122 difficult routes available. The region's characteristic rolling hills, such as those leading to Coombe Hill and Ivinghoe Beacon, provide significant inclines and rewarding views, making for a strenuous and satisfying run.
Yes, many of the running routes in the area are circular, offering convenient starting and ending points. An example is the The Lee Village Green – The Cock and Rabbit loop from The Lee, which provides a moderate 4.3-mile path through village scenery and countryside.
The running routes in Cholesbury-Cum-St Leonards are rich with historical and natural sights. You might pass by the impressive Iron Age hillfort of Cholesbury Camp, enjoy panoramic views from Coombe Hill Viewpoint and Boer War Memorial, or take in the vistas from Ivinghoe Beacon. Ancient woodlands like Red Cedar Woods also offer scenic stretches.
Many of the footpaths and trails in Cholesbury-Cum-St Leonards, particularly those through woodlands and open commons like Hawridge and Cholesbury Commons, are suitable for dogs. However, it's always advisable to keep dogs under control, especially when passing through livestock areas or nature reserves, and to check local signage for any specific restrictions.
Yes, the region is known for its charming villages, and many routes are designed to start or finish near local pubs, offering a perfect opportunity for refreshment after your run. The Rushmore Lane – Hen & Chickens Pub loop from Chesham is one such example, incorporating a local pub into its route.
Cholesbury-Cum-St Leonards offers enjoyable running conditions throughout much of the year. Spring and summer bring vibrant wildflowers to the chalk grasslands and lush greenery to the woodlands. Autumn provides stunning foliage, while winter runs can be crisp and invigorating, especially through the sheltered ancient woodlands. Always check local weather conditions before heading out.
While many routes are shorter loops, the extensive network of paths allows for longer runs by combining sections. For example, the Running loop from Chesham covers over 11 km, offering a good option for those looking for a more extended workout.
Yes, the area offers many family-friendly options, particularly the easier routes through woodlands and commons. These paths are generally well-maintained and provide a safe and enjoyable environment for families to run or walk together, allowing everyone to experience the natural beauty of the Chiltern Hills.
For additional details on the local area, including Hawridge and Cholesbury, you can visit resources like visitchesham.org.uk, which provides insights into the region's offerings.


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