Cholesbury-Cum-St Leonards
Cholesbury-Cum-St Leonards
4.6
(208)
3,105
riders
235
rides
No traffic touring cycling routes around Cholesbury-Cum-St Leonards are set within the Chiltern Hills Area of Outstanding Natural Beauty. The region features varied terrain, including rolling hills, ancient woodlands, and chalk grasslands. Cyclists can expect routes traversing extensive beech forests, alongside oak, ash, and hazel trees, with natural ponds fed by springs adding to the rural scenery. The landscape offers engaging and varied terrain for touring cyclists.
Last updated: May 19, 2026
5.0
(1)
4
riders
14.8km
00:54
110m
110m
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
4
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.

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2
riders
17.9km
01:21
240m
240m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
1
riders
Easy bike ride. Great for any fitness level. Mostly paved surfaces. Suitable for all skill levels.
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Popular around Cholesbury-Cum-St Leonards
Best cycling cafe in the area. Great views and coffee.
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Today, only a few of them are still in operation in their original function; instead, they often serve as mere technical and historical monuments to a long tradition of craftsmanship: The heavy millstones inside were moved solely by the power of the wind, for example, grinding grain into flour (so-called grain mills) or pressing oil from fruits (e.g., olives) (so-called oil mills). Thus, these old windmills are the best proof that people were clever enough to harness the power of the wind several centuries ago – long before the discovery of electricity and the inventions that followed it.
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Great cycling themed cafe with a large terrace and plenty of bike space. Well worth a stop off on a Chilterns ride.
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A decent coffee and cake stop. Bike workshop too for those who are local!
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Footpath closed and train viaduct visible in the distance in 2024
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Café is still around in 2024. :) It's got a nice terrace at the back (incl. bike racks).
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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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A lovely run on gravel bike. I the summer whendry it is fast and flowing
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There are over 200 dedicated no-traffic touring cycling routes in Cholesbury-Cum-St Leonards. These routes cater to various skill levels, with 61 easy, 115 moderate, and 71 difficult options.
The no-traffic routes in Cholesbury-Cum-St Leonards traverse the varied terrain of the Chiltern Hills AONB. You'll encounter rolling hills, expansive meadows, and ancient woodlands, including beech forests and areas with oak, ash, and hazel. While generally quiet, some routes may include wide tracks or bridleways that are shared with walkers or horse riders.
Yes, there are several easy, circular no-traffic routes. For instance, the View of Grim's Ditch – Pavis Wood Singletrack loop from Cholesbury-cum-St Leonards is an easy 8.9 km ride that offers a glimpse of historical earthworks and woodland paths. Another option is the Hawridge Windmill – Chiltern Velo Café loop from Cholesbury, an easy 14.8 km route.
Many no-traffic routes offer scenic views and pass by notable natural features and historical landmarks. You might encounter ancient woodlands like Pavis Woods or Drayton Woods, old hedgerows, and natural ponds. For expansive vistas, consider routes that offer views towards Coombe Hill Viewpoint or Ivinghoe Beacon. Some routes also pass by historical sites such as Grim's Ditch.
Yes, many of the easy-grade no-traffic routes are suitable for families. These often follow quiet country paths and wide tracks, avoiding main roads. The Dundridge Manor Bridleway – Chiltern Link Forest Path loop from Cholesbury-cum-St Leonards is an easy 11 km option that explores woodlands and bridleways, providing a safe and enjoyable experience for families.
While many routes are on quiet paths, the suitability for dogs depends on the specific trail and local regulations. Generally, dogs are welcome on public bridleways and footpaths if kept under control. Always check for signs regarding dog access, especially in nature reserves or private land. Ensure your dog is comfortable with cycling speeds and other trail users.
The area is well-equipped with cyclist-friendly stops. The Chiltern Velo Café and Bike Workshop in Hawridge is specifically geared towards cyclists, offering a welcoming spot with outdoor seating. Historic pubs like The Full Moon in Cholesbury or The Rose and Crown in St Leonards also provide excellent rest stops and refreshments. Some routes, like the Dundridge Manor Bridleway – Chiltern Velo Café loop from Cholesbury-cum-St Leonards, are designed to include a café stop.
Spring and autumn are often considered the best times for cycling in Cholesbury-Cum-St Leonards. In spring, the bluebell woods are in bloom, and the weather is generally mild. Autumn offers beautiful foliage. Summer can be pleasant, but some paths might be busier. Winter cycling is possible, but be prepared for potentially muddy sections on unpaved tracks and colder temperatures.
While the immediate area is known for its woodlands and hills, some routes may lead to or pass near local ponds. For larger water features, you might find routes that extend towards highlights like Marsworth Reservoir or Shardeloes Lake, which are slightly further afield but accessible within the wider Chilterns network.
The area is highly rated by the komoot community, with an average score of 4.6 stars from 189 ratings. Reviewers often praise the tranquility of the no-traffic routes, the picturesque rolling hills, and the charm of cycling through ancient woodlands and past historic villages. The well-maintained network of country paths and the availability of cyclist-friendly cafes are also frequently highlighted.
Public transport options to Cholesbury-Cum-St Leonards are limited, making car access more common for cyclists bringing their bikes. However, local bus services connect to nearby towns like Chesham, which has a Metropolitan Line underground station. From Chesham, you could cycle to the starting points of some routes, though this might involve busier roads initially. Always check bus routes and bike carriage policies in advance.
Parking is generally available in or near the villages of Cholesbury and St Leonards. Look for designated village car parks or consider parking responsibly in areas that do not obstruct local residents or access points to trails. Many routes start from points with informal parking opportunities, particularly near popular pubs or the Chiltern Velo Café.


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