4.6
(3280)
20,703
hikers
24
hikes
Hikes around Cholesbury-Cum-St Leonards explore the rolling hills and ancient woodlands of the Chiltern Hills Area of Outstanding Natural Beauty. The landscape is characterized by extensive beech forests, open meadows, and chalk grasslands. Many trails incorporate historical sites, including the well-preserved Iron Age earthworks of Cholesbury Camp.
Last updated: May 3, 2026
5.0
(2)
22
hikers
Easy hike. Great for any fitness level. Easily-accessible paths. Suitable for all skill levels.
4.0
(3)
14
hikers
8.21km
02:10
70m
70m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

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4.3
(4)
11
hikers
9.46km
02:31
100m
100m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
2
hikers
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
20.0km
05:20
220m
220m
Hard hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.
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Popular around Cholesbury-Cum-St Leonards
They advertised on Sunday's that they don't just do roast dinners but also sandwiches, perfect for a pre or post hike lunch. Excellent garden when it's warm and a covered terrace when it's cold. Good to book!
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St Mary's Church was first mentioned in 1227. In the 19th century, it fell into disrepair, and was subsequently rebuilt in 1856 by the architect William White. He used flint-and-brick materials and gave the church a style specific to the 1850s known as "constructional polychromy" (the practice of architectural decoration using a variety of colours). The tower, I find, is particularly attractive. Worth stopping at: it's a lovely little church.
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The history of the village of St Leonard's is tightly connected with the chapel of Leonard's - and this dates back to the 12th century. The present church, however, was built in the 15th century. As many such places, it has had a tumultuous history. For instance, after the Dissolution of the Monasteries, the chapel continued being used and Queen Elizabeth inquired in 1586 into why the chapel and the lands had not reverted to the Crown. The church feel into disrepair in the 17th century. What can be seen today is in the simple Queen Anne style, and was rebuilt around 1700s. The whitewashed walls are striking and give the church a unique look. In the winter, it can look brilliant after snow, and in the spring, when the snowdrops come up (plenty of them in the church grounds), it also looks terrific.
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This green walk begins in one forest and ends in another, with gorgeous green views throughout of the valley of the dry valley of Asheridge Bottom. The sweeping valley view should take your breath away.
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This is a nice and long path and track between Cholesbury and Chesham. A beautifully varied one, too: woodlands, views of rolling hills and fields, meadows, cattle... essentially, everything good that the British countryside has to offer!
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This is an impressive structure (although it's not easy to get up close to it), an imposing sight over the street. It's disused windmill. The first windmill here was built in the 17th century, but later a smock mill was constructed in 1863 by the Norwich Wind and Steam Company. Eventually, the building was converted into a private residence in the early 20th century. It's a Grade II listed building.
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This is a classic country pub in an achingly pretty village. There's a lovely beer garden and delicious food in the restaurant. The pub is just a short walk from the Chiltern Heritage Trail and makes for an excellent pitstop or objective on a walk in the hills here.
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I wish I lived in a windmill! What a fantastic structure. It might be a house or a studio, I can't really tell from the roadside.
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Yes, the area is well-suited for family walks. The landscape features many gentle paths through woodlands and across open commons, which are perfect for shorter legs. You'll find a dozen easy-rated trails, typically on well-trodden paths with minimal elevation changes, making for a relaxed day out.
Absolutely. The extensive network of footpaths through the Chilterns' woodlands and fields is great for dog walking. However, please be mindful of local wildlife and any livestock in the fields. It's best to keep your dog on a lead, especially in nature reserves or areas with ground-nesting birds.
Most hikes feature a pleasant mix of terrain characteristic of the Chiltern Hills. Expect to walk on shaded woodland tracks under magnificent beech trees, cross open chalk grasslands with wide-ranging views, and follow paths along quiet country lanes. The hills are rolling rather than steep, offering gentle climbs.
Yes, the vast majority of the walking routes in this area are circular. They are designed to bring you back to your starting point, which is often a village, a common, or a local pub. This makes planning your hike straightforward, especially if you are arriving by car.
The most significant historical site is Cholesbury Camp, a large and well-preserved Iron Age hillfort. Many walks incorporate its impressive earthwork ramparts. You can also find St. Lawrence's Church uniquely situated inside the fort. Some longer routes may also pass sections of Grim's Ditch, another ancient earthwork.
Many trails conveniently start and end near traditional country pubs. For a rewarding walk, you could try the Cholesbury Windmill and Asheridge Bottom loop from Cholesbury β Chiltern Hills. It begins in the village, making it easy to enjoy refreshments at a local pub like The Full Moon after your hike.
Getting to the area by public transport can be challenging as the villages are quite rural. The nearest train stations are in Tring or Wendover, both several miles away. From there, you would likely need to take a local bus service, which may be infrequent, or a taxi to reach the trailheads.
There is no single large car park for the area. Most hikers find informal on-street parking in villages like Cholesbury or Hawridge, particularly near the commons. Please park considerately, ensuring you do not block residents' access or narrow country lanes. Some local pubs may also allow parking for patrons.
For some of the best panoramic views in the Chilterns, head towards Coombe Hill. At 852 feet, it's the highest viewpoint in the region, offering stunning vistas over the Aylesbury Vale. Nearby Pitstone Hill is another excellent spot, known for its pristine chalk grassland and far-reaching views.
Yes, a section of The Ridgeway National Trail, an ancient path that's been used for over 5,000 years, runs near the parish. You can easily join parts of this famous trail on some of the longer local loops, such as the St Mary's Church and Pavis Wood loop from Cholesbury β Chiltern Hills, which connects with it.
The area is highly rated by the komoot community. Reviewers often praise the beautiful ancient beech woodlands, the peace and quiet of the trails, and the fascinating history of Cholesbury Camp. The mix of shaded woods and open hillsides is frequently mentioned as a highlight.
You can explore over 20 hiking routes around Cholesbury-Cum-St Leonards. The collection includes about a dozen easy walks perfect for a casual stroll, 11 moderate routes for a more substantial hike, and one difficult trail for those seeking a full-day challenge.


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