Cholesbury-Cum-St Leonards
Cholesbury-Cum-St Leonards
4.6
(283)
1,027
riders
129
rides
Mountain biking around Cholesbury-Cum-St Leonards offers a network of trails through the rolling hills and woodlands of the Chilterns. The landscape features a mix of ancient forests, open fields, and varied elevations suitable for mountain biking. Many routes follow established bridleways and country paths, providing diverse terrain. This area is characterized by its natural beauty and accessible trails for various skill levels.
Last updated: July 7, 2026
4.5
(37)
133
riders
43.5km
03:38
720m
720m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.
4.9
(25)
45
riders
25.5km
01:58
320m
320m
Moderate mountain bike ride. Good fitness required. Advanced riding skills necessary.

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4.7
(3)
14
riders
39.6km
03:14
600m
600m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
4
riders
21.9km
01:49
330m
330m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
5.0
(1)
4
riders
29.7km
01:54
280m
280m
Easy mountain bike ride. Great for any fitness level. Suitable for all skill levels.
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Popular around Cholesbury-Cum-St Leonards
Final part of the route is quite narrow and plants have overgrown further narrowing the path
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This is a great single track that goes up through Pond Wood, past Longdown Farm, and onwards into Pulpit Wood. It can be muddy in bad weather. It is an established trail though and forms part of the Icknield Way Trail, so beware of hikers and other path users.
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This path overlooking a valley was rideable on a gravel bike in peak-summer, even while it had been drizzling for the last hour.
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On a gravel bike, one packed for a multi-day exploration of the Icknield Way, this was one of the more challenging, slow-going segments due to the narrowness and roots.
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There is a lovely little weir on the River Chess here that's worth stopping by. Also, on the same pond, you will see stepping stones (called Steps of Heaven by some) if you'd like to walk across! A good few years ago, I used to live in the street right next to these ponds, so I can vouch for the fact that this is a great place to spend some time at, particularly in the summer.
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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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There are over 130 mountain bike trails around Cholesbury-Cum-St Leonards. These routes cater to various skill levels, from easy rides to more challenging options, exploring the diverse landscapes of the Chilterns.
Yes, Cholesbury-Cum-St Leonards offers a good selection of easy mountain bike trails. There are 53 easy routes available, perfect for beginners or families looking for a less strenuous ride. An example is the Temperance Hall, Chesham β St Leonard's Church loop from Chesham, which is 29.7 km long and classified as easy.
For experienced riders seeking a challenge, there is one difficult mountain bike trail available. Additionally, many of the 80 moderate routes offer varied terrain and elevation changes that can provide a good workout. The region's rolling hills and woodlands ensure a dynamic riding experience.
Yes, many of the mountain bike trails in the area are designed as loops, allowing you to start and finish at the same point. Examples include the View from Whiteleaf Hill β Pulpit Wood singletrack loop from Dancersend and the Hen & Chickens Pub β Bunn's Lane Public Bridleway loop from Chesham.
The terrain around Cholesbury-Cum-St Leonards is characterized by rolling hills, dense woodlands, and open fields. Trails often follow established bridleways and country paths, offering a mix of surfaces from dirt tracks to gravel, with varied elevations typical of the Chilterns.
The trails often pass through scenic natural areas and near historical landmarks. You might encounter viewpoints like the Coombe Hill Viewpoint and Boer War Memorial, or natural features such as Ivinghoe Beacon and Pitstone Hill. The View of Bacombe Hill β Coombe Hill Descent loop from Wigginton offers views of Bacombe Hill.
The area is highly rated by the komoot community, with an average score of 4.7 stars from over 260 reviews. Mountain bikers frequently praise the diverse terrain, the natural beauty of the Chilterns, and the well-maintained network of bridleways that make for enjoyable rides.
Generally, mountain biking on public bridleways and byways in the Cholesbury-Cum-St Leonards area does not require specific permits. However, it's always advisable to check local signage and respect private land. Stick to designated paths to ensure access for all users.
Spring and autumn often provide the most pleasant conditions for mountain biking in Cholesbury-Cum-St Leonards, with milder temperatures and beautiful scenery as the woodlands change. Summer can also be excellent, though trails might be busier. Winter rides are possible, but some paths may be muddy or slippery, especially after heavy rain.
Many public bridleways and country paths in the Chilterns are dog-friendly, allowing you to bring your canine companion along. However, dogs should be kept under control, especially around livestock, and on a lead in certain areas. Always check specific route details and local regulations for any restrictions.
Many trailheads and popular starting points in and around Cholesbury-Cum-St Leonards offer parking facilities, often in village car parks or designated lay-bys. It's recommended to check the starting points of individual routes on komoot for specific parking information and availability.
While popular routes can see more traffic, the extensive network of over 130 trails means it's often possible to find quieter paths, especially on weekdays or by exploring some of the less-trafficked moderate routes. The Hale Wood and Barn Wood β Crong Valley Path loop from Wigginton offers a chance to explore woodlands away from the busiest spots.


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