4.7
(37)
1,532
riders
72
rides
Road cycling routes around Chesham are situated within the Chiltern Hills Area of Outstanding Natural Beauty, offering diverse terrain for cyclists. The region is characterized by undulating hills, extensive woodlands, and chalk downland, providing varied experiences. The Chess Valley offers gentler landscapes, while elevated points like Ivinghoe Beacon provide views. This combination of features creates a network of routes suitable for different fitness levels.
Last updated: May 17, 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
(2)
95
riders
48.2km
02:19
500m
500m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

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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.
51
riders
33.8km
01:26
220m
220m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Best cycling cafe in the area. Great views and coffee.
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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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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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Chenies climb is a hard climb and if you like climbing you will probably do it easily
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A decent coffee and cake stop. Bike workshop too for those who are local!
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Cafรฉ is still around in 2024. :) It's got a nice terrace at the back (incl. bike racks).
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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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Chesham is nestled within the Chiltern Hills Area of Outstanding Natural Beauty, so you can expect a diverse and undulating terrain. This includes both challenging climbs and rewarding descents through picturesque woodlands and chalk downland. The Chess Valley offers gentler landscapes, while elevated points like Ivinghoe Beacon provide panoramic views.
There are over 70 road cycling routes available around Chesham on komoot, catering to various skill levels. This includes 30 easy routes, 36 moderate routes, and 6 more challenging options for experienced cyclists.
Yes, for families or those seeking a more relaxed ride, the 5-mile Phoenix Trail offers a traffic-free path along a former railway line between Thame and Princes Risborough, providing views of the Chiltern Hills. Additionally, komoot offers 30 easy routes in the Chesham area, such as the Temperance Hall, Chesham โ A Little Street Kitchen loop from Chesham, which is 24.0 miles (38.7 km) and less strenuous.
Many routes offer scenic views and pass by interesting landmarks. You can find breathtaking panoramic views from elevated points like Ivinghoe Beacon. Other notable attractions include the Coombe Hill Viewpoint and Boer War Memorial, the historic Bridgewater Monument, and the charming Aldbury Village. Some routes also pass by beautiful lakes such as Shardeloes Lake.
Chesham and the surrounding hilltop villages are cyclist-friendly, with many pubs and cafes serving as excellent pitstops. Notably, the Chiltern Velo Cafรฉ & Bike Workshop in Hawridge offers a cafรฉ, outdoor terrace, and bike servicing and repair facilities, making it a popular stop for cyclists.
Yes, the Chiltern Hills provide plenty of challenging climbs. For instance, the Aldbury Village Pond โ Ivinghoe Beacon Climb loop from Chesham is a moderate 56.5 miles (90.9 km) route with significant elevation gain, leading through varied landscapes including the Ivinghoe Beacon area. There are 6 difficult routes available on komoot for those seeking a greater challenge.
The Chiltern Hills offer beautiful scenery year-round. Spring and autumn provide pleasant temperatures and vibrant landscapes, while summer allows for longer days. Even in winter, many routes are accessible, though conditions may vary. Always check local weather before heading out.
Chesham is accessible by public transport. Non-folding bicycles can be transported on the Metropolitan line outside of peak times, offering convenient access to Chesham from London. This makes it easy to start your cycling adventure directly from the town.
Yes, many of the road cycling routes around Chesham are circular, allowing you to start and end in the same location. An example is The Royal Standard pub loop - Chesham to Winchmore Hill, a 36.4 miles (58.5 km) moderate trail that navigates the rolling terrain of the Chilterns.
The road cycling routes in Chesham are highly rated by the komoot community, with an average score of 4.6 stars from over 36 reviews. More than 1500 road cyclists have used komoot to explore Chesham's varied terrain, often praising the diverse landscapes and the rewarding climbs and descents.
Chesham offers various parking options, particularly in the town center, which can serve as a convenient starting point for many routes. For specific trailheads or routes, it's advisable to check the individual route details on komoot for recommended parking areas.
Yes, Chesham is a hub for significant cycling routes. The Chilterns Cycleway, a 170-mile (273km) circular route, winds through the region, with sections traversing Chesham and surrounding villages. Additionally, National Cycle Route 57, a 63-mile (101km) Sustrans route connecting the Cotswolds to Welwyn Garden City, passes directly through Chesham.


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