Cholesbury-Cum-St Leonards
Cholesbury-Cum-St Leonards
4.5
(257)
10,542
riders
523
rides
Road cycling around Cholesbury-Cum-St Leonards offers diverse landscapes within the Chiltern Hills Area of Outstanding Natural Beauty. The region is characterized by rolling hills, expansive ancient woodlands, open meadows, and distinctive chalk grasslands. Road cycling routes feature mostly paved surfaces with varying elevation gains, catering to different fitness levels. The topography includes numerous hills and scenic viewpoints across the Aylesbury Vale.
Last updated: July 14, 2026
5.0
(3)
156
riders
39.2km
01:57
380m
380m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
111
riders
90.9km
04:06
840m
840m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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5.0
(2)
97
riders
48.1km
02:18
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
80
riders
55.6km
02:45
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
82
riders
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Cholesbury-Cum-St Leonards
This is a short tough climb which demands your full attention. Loved it.
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Beautiful forrest vibe lane. Makes you feel close to nature. Watch out for the potholes, especially if you don't have a photochromic lenses as it gets darks with tall trees around.
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This was on my route unexpectedly. Left my mouth open for a bit. Very beautiful.
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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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As English villages in the Chiltern Hills go, this one is one of the most attractive. This is the kind of place I tend to think of when I read Agatha Christie's Miss Marple. The village name is Anglo-Saxon and means "a woodland clearing". Another little fun fact: Sir Arthur Lasenby Liberty (1843–1917), proprietor of the famous Regent Street (London) store, Liberty & Co., lived here and built a Manor house here in 1900. He was associated with the Art Nouveau style.
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Ashridge house and the surrounding woods are a great spot for a ride or a run. Elizabeth 1 spent parts of her childhood at the house.
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The region, nestled within the Chiltern Hills, features diverse landscapes with rolling hills, expansive ancient woodlands, open meadows, and distinctive chalk grasslands. Routes primarily use paved surfaces, offering varying elevation gains from gentle gradients to significant climbs, catering to different fitness levels.
Yes, there are plenty of options for all skill levels. Over 200 easy road cycling routes are available. For example, the Temperance Hall, Chesham – A Little Street Kitchen loop from Chesham is an easy 24-mile route with gentle gradients, perfect for a relaxed ride.
For those seeking a challenge, the area offers routes with notable elevation gains. A popular moderate option is the Aldbury Village Pond – Ivinghoe Beacon Climb loop from Chesham, a 56.5-mile path that includes significant climbs and rewards cyclists with extensive views from Ivinghoe Beacon.
The region is rich in scenic spots and historical landmarks. You can enjoy breathtaking panoramic vistas from Coombe Hill Viewpoint and Boer War Memorial, the highest point in the Chilterns. Ivinghoe Beacon also offers extensive views. Additionally, you might encounter the impressive Iron Age hillfort, Cholesbury Camp, or the prehistoric earthwork Grim's Ditch along various routes.
Many of the road cycling routes in Cholesbury-Cum-St Leonards are designed as loops, allowing you to start and finish at the same point. For instance, the Aldbury Village Green and Pond – Temperance Hall, Chesham loop from Chesham is a 30.3-mile circular trail through varied terrain.
The diverse landscapes, including ancient woodlands and open meadows, make spring and autumn particularly appealing for road cycling. Spring brings blooming wildflowers, while autumn offers vibrant foliage. Summer is also excellent, though routes can be more exposed to the sun. Always check local weather conditions before heading out.
Yes, the area is cyclist-friendly with establishments like the Chiltern Velo Café and Bike Workshop in nearby Hawridge. Many routes are designed to pass through villages or near local pubs, providing convenient stops for refreshments and meals. The region is known for routes often starting or finishing at local pubs.
The road cycling routes in Cholesbury-Cum-St Leonards are highly rated by the komoot community, with an average score of 4.5 stars from over 180 reviews. Cyclists often praise the varied terrain, scenic views, and the network of routes that cater to different ability levels.
Absolutely. The region is rich in ancient woodlands, such as Captains Wood, areas along Kiln Lane, and Buckland, Pavis and Drayton Woods. The distinct Red Cedar Woods Path also offers a unique woodland cycling experience, providing shaded and picturesque sections for your ride.
Yes, areas like Pitstone Hill and Coombe Hill are designated Sites of Special Scientific Interest (SSSI) due to their chalk grasslands, which are home to rare wildflowers, numerous butterfly species, and a variety of birdlife. Cycling through or near these areas offers opportunities for nature observation.
Route lengths vary significantly to suit different preferences and fitness levels. You can find shorter loops around 24 miles, such as the Temperance Hall, Chesham – A Little Street Kitchen loop, up to longer rides like the The Lee Village Green – Bryants Bottom Road loop from Chesham which covers about 34.5 miles (55.5 km).


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