4.8
(33)
370
riders
47
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: October 25, 2026
5.0
(1)
33
riders
49.7km
03:07
510m
510m
Hard bike ride. Very good fitness required. Mostly paved surfaces.
16
riders
95.0km
05:56
920m
920m
Hard bike ride. Very good fitness required. You may need to push your bike for some segments of this route.

4.7
(3)
19
riders
29.2km
01:51
280m
280m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
5.0
(7)
27
riders
40.6km
02:32
310m
310m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
5.0
(1)
19
riders
50.1km
03:06
440m
440m
Moderate bike ride. Good fitness required. Mostly paved surfaces.
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Best cycling cafe in the area. Great views and coffee.
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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.
0
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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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0
CafΓ© is still around in 2024. :) It's got a nice terrace at the back (incl. bike racks).
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0
The striking clock tower in the centre of Chesham looks older, but it's not: it was built in 1992! However, it's the tower that's new, not the clock itself, which used to be a part of Chesham Town Hall.
1
0
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 CafΓ© β Pavis Wood Singletrack loop from Chesham. This route covers about 50 km (31 miles) and includes a stop at the cyclist-friendly Chiltern Velo CafΓ©, 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 CafΓ© & 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 β 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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