4.7
(37)
1,534
riders
39
rides
No traffic road cycling routes around Chesham benefit from its location within the Chilterns National Landscape, an Area of Outstanding Natural Beauty. The region is characterized by undulating terrain, quiet country lanes, and dense woodlands, offering varied landscapes for road cyclists. The scenic Chess Valley, with the River Chess, adds to the natural features, providing a diverse environment for exploration. This area presents a mix of challenging climbs and rewarding descents suitable for different cycling preferences.
Last updated: May 19, 2026
4.3
(7)
36
riders
58.5km
02:40
460m
460m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(1)
104
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)
95
riders
48.2km
02:19
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
82
riders
55.6km
02:45
610m
610m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
51
riders
53.2km
02:20
350m
350m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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This is a short tough climb which demands your full attention. Loved it.
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Amazing pub, with an amazing history and even more beautiful walks around like Coleshill and Penn.
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Chenies climb is a hard climb and if you like climbing you will probably do it easily
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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 (1843β1917), 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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This magnificent, charming, 15th-century pub holds the impressive title of the oldest pub in Britain! With its nooks and crannies, gnarled timbers, worn flagstones and carved oak panels, it'll be sure to charm you. You may even recognise it from a few films and TV shows, including Hot Fuzz.
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Komoot offers a selection of 39 no-traffic road cycling routes around Chesham, ranging from easy to moderate difficulty. This includes 20 easy routes and 19 moderate routes, ensuring options for various fitness levels.
Yes, Chesham offers 20 easy-rated no-traffic road cycling routes, perfect for beginners or those seeking a relaxed ride. An example is the Temperance Hall, Chesham β A Little Street Kitchen loop from Chesham, which is an easy 38.7 km ride with minimal elevation gain.
While this guide focuses on no-traffic routes, many of the moderate routes in the Chilterns still offer significant climbs. For example, the Aldbury Village Pond β Ivinghoe Beacon Climb loop from Chesham is a moderate 90.9 km route with over 800 meters of elevation gain, taking you towards the challenging terrain around Ivinghoe Beacon.
The routes wind through the stunning Chilterns National Landscape, an Area of Outstanding Natural Beauty. You'll experience rolling countryside, dense woodlands, and serene river valleys like the Chess Valley, known for its diverse wildlife. Many routes offer picturesque views and pass by natural highlights such as the River Chess Stepping Stones and Weir.
Yes, Chesham's rich history is visible along many routes. You might pass through the town's Old Town with its timber-framed buildings or near historic sites like Chenies Manor House. The Aldbury Village Green and Pond β Temperance Hall, Chesham loop from Chesham takes you past the charming Aldbury Village, known for its historic character.
The region is well-equipped for cyclists. Many routes pass through charming villages with pubs and cafes. A notable stop is the Chiltern Velo CafΓ© & Bike Workshop in Hawridge, a popular spot for refreshments, repairs, and advice. Routes like The Royal Standard pub loop - Chesham to Winchmore Hill often include stops at local establishments.
Yes, Chesham is accessible via the Metropolitan line. Non-folding bicycles can be transported on the Metropolitan line outside of peak hours, making it convenient to reach Chesham and start your ride directly from the town.
The Chilterns are beautiful year-round, but spring and autumn offer particularly pleasant conditions with mild weather and stunning natural colours. Summer is also popular, though routes can be busier. Winter rides are possible, but be prepared for colder temperatures and potentially wet conditions.
The komoot community highly rates the road cycling experience in Chesham, with an average score of 4.6 stars from 36 ratings. Reviewers often praise the quiet country lanes, the beautiful Chilterns scenery, and the variety of routes suitable for different fitness levels, making it ideal for no-traffic rides.
Yes, among the 20 easy routes, you can find shorter options. For instance, the Temperance Hall, Chesham β A Little Street Kitchen loop from Chesham is an easy 38.7 km ride, providing a good option for a shorter, traffic-free experience.
Many of the routes in this guide utilize the quiet country lanes that crisscross the Chilterns. The Chilterns Cycleway and National Cycle Route 57, which pass through Chesham, are specifically designed to use these low-traffic roads, connecting charming villages like Cholesbury, Hawridge, and Latimer.
Chesham is a well-established hub for cyclists, popular with both individual riders and clubs. While this guide focuses on routes, you can often find information about local cycling groups and events through community resources or local bike shops. For more local cycling information, you might find resources on the Visit Chesham website.


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