4.8
(30)
394
riders
51
rides
Touring cycling routes around Chesham are set within the Chiltern Hills National Landscape, characterized by rolling countryside, dense woodlands, and river valleys. The terrain is undulating, featuring both challenging climbs and descents, with many routes utilizing quiet country lanes. The region offers a mix of scenic on-road cycling and some off-road stretches, providing varied experiences for cyclists.
Last updated: April 26, 2026
5.0
(1)
26
riders
49.6km
03:08
530m
530m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
16
riders
94.9km
05:52
900m
900m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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5.0
(7)
26
riders
40.6km
02:32
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(1)
16
riders
50.1km
03:09
440m
440m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
5.0
(2)
16
riders
43.8km
02:49
390m
390m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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Ashridge Estate is a large area of ancient trees, chalk downland and meadows in an area of Outstanding Natural Beauty. It's been managed by the National Trust since 1926.
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Really nice gentle climb up the hill on a great surface.
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Lovely little town, had a roast dinner here in a Japanese restaurant of all things!
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A decent coffee and cake stop. Bike workshop too for those who are local!
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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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There are over 50 touring cycling routes available around Chesham, offering a wide range of options for exploring the Chiltern Hills National Landscape.
Touring cycling in Chesham is characterized by undulating terrain with both challenging climbs and descents, set within the rolling countryside and dense woodlands of the Chiltern Hills. Routes often utilize quiet country lanes, with some sections including off-road stretches.
The routes around Chesham cater to various fitness levels. You'll find approximately 16 easy routes, 24 moderate routes, and 12 difficult routes, ensuring options for different abilities and preferences.
Yes, for a moderate challenge, consider the Chiltern Velo Café – Pavis Wood Singletrack loop from Chesham. This route covers about 50 km (31 miles) and includes a stop at the cyclist-friendly Chiltern Velo Café, offering a pleasant ride through varied terrain.
Many touring cycling routes around Chesham are circular, allowing you to start and finish in the same location. The wider Chilterns area, including sections of the 170-mile Chilterns Cycleway, is designed with circular loops in mind, making it easy to plan round trips.
The routes often pass through the scenic Chess Valley, where you might spot wildlife like kingfishers and water voles. Nearby attractions include the Coombe Hill Viewpoint, offering panoramic views, and the historic Ashridge House. You can also explore charming villages like Aldbury, which features Aldbury Village itself.
Yes, the region is well-equipped for cyclists. The Chiltern Velo Café & Bike Workshop in Hawridge is a popular stop, offering refreshments and bike services. Many of the charming hilltop villages surrounding Chesham also feature welcoming pubs and cafes.
The area is highly rated by the komoot community, with an average score of 4.8 stars from over 30 reviews. Reviewers often praise the diverse terrain, the beauty of the Chiltern Hills, and the well-maintained country lanes that make for enjoyable rides.
Absolutely. The Chesham Clock Tower – Grove's Windmill, Coleshill loop from Chesham is a moderate 43.7 km (27.2 miles) route that takes you through picturesque countryside and past historic points of interest like Grove's Windmill and the village of Coleshill.
Chesham is enjoyable for touring cycling throughout much of the year. Spring brings beautiful bluebells to ancient woodlands like Cowcroft Woods, while autumn offers stunning foliage. Summer provides longer daylight hours, and milder days in winter can also be pleasant, though some unsurfaced sections might be muddy.
Yes, Chesham is accessible by public transport. Non-folding bicycles can be transported on the Metropolitan line outside peak hours, allowing you to start your cycling adventures directly from Chesham.
Many routes in the Chilterns offer expansive views. The nearby Coombe Hill Viewpoint, the highest point in the Chilterns, provides panoramic vistas over the Aylesbury Vale and beyond, and can be incorporated into longer rides.


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