4.5
(467)
18,430
riders
187
rides
Road cycling around Chepping Wycombe is characterized by its undulating terrain within the Chiltern Hills, an Area of Outstanding Natural Beauty. The region features a mix of chalk escarpments, valleys, and extensive woodlands, providing varied landscapes for cyclists. Routes often traverse the scenic Chilterns and incorporate sections near the River Thames Valley, offering diverse gradients and views. The area's topography supports a range of no traffic road cycling routes suitable for different fitness levels.
Last updated: October 12, 2026
18
riders
36.4km
01:46
330m
330m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
12
riders
59.1km
02:50
570m
570m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

5.0
(1)
6
riders
29.8km
01:30
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
4.1
(9)
3
riders
30.0km
01:34
290m
290m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Truly a village that is steeped in olde worlde charm. Some great restaurants and pubs. The history seeps through its pores. The Kings Arms Hotel & The Crown Hotel & Pub in Amersham, was the set of a scene the 4 Weddings and a funeral movie.
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In the summer there are tours for Β£3 donation from 2pm on Sunday
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Beautiful town and perfect to finish off hike/ walking trail, great choice of CafΓ©, try sitting outside @ Amersham House for coffee/ brunch
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Stunning little pond on Penn Common with a charming pub nearby. A great place to stop for a break, or just to enjoy the view as you ride past. Especially beautiful as the sun is going down.
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Winchmore Hill goes back to the 12th century: there used to be a small settlement here supporting farms grouped around a Common and a pond (those were the days). In 1958, the pond was filled in, but luckily the Common is still here, on the edge of what used to be Wycombe Heath: 4,000 acres of open common land providing grazing for animals and material for firewood. It's a lovely hamlet. There is a great information board, from which you can learn more about the history of the place. And a good pub in a village can never be wrong! - so make sure you make a stop at The Plough!
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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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Old Amersham is a delightfully charming town filled with historic architecture, independent shops, cafΓ©s, and restaurants, and a weekly market that dates back to the 13th-century!
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There are over 180 dedicated no-traffic road cycling routes around Chepping Wycombe. These routes traverse the beautiful Chiltern Hills and offer a range of difficulties, from easy rides to more challenging ascents.
The routes in Chepping Wycombe, particularly those within the Chiltern Hills, feature undulating terrain with a mix of challenging climbs and gentler sections. You can expect well-paved surfaces, offering a classic road cycling experience amidst scenic landscapes.
Yes, Chepping Wycombe offers over 60 easy, traffic-free road cycling routes perfect for beginners or those seeking a relaxed ride. An example is the Penn Common Pond β Penfold Lane loop from Gomm Valley, which covers approximately 29.8 km with moderate elevation gain.
Absolutely. For those looking for a longer ride, the Bryants Bottom Road β The Lee Village Green loop from Penn offers a moderate 59.1 km route with over 560 meters of elevation gain, providing a good challenge while keeping you away from heavy traffic.
Many routes pass through or near significant natural features and landmarks. You might cycle past parts of the River Thames Valley, through extensive woodlands like Gomm's Wood, or near the chalk grasslands of Sands Bank Local Nature Reserve. Historical sites such as Hughenden Manor and the Dashwood Mausoleum are also accessible in the wider area.
Yes, many of the no-traffic road cycling routes around Chepping Wycombe are circular, allowing you to start and finish at the same point. For instance, the Lacey Green Windmill β Winchmore Hill loop from Gomm Valley is a circular route covering about 36.4 km.
The komoot community highly rates the road cycling experience in Chepping Wycombe, with an average score of 4.5 stars. Cyclists often praise the region's diverse landscapes, the quiet roads, and the opportunity to explore charming villages and natural beauty within the Chiltern Hills.
Chepping Wycombe is well-connected by public transport, making it feasible to reach many starting points for cycling routes. High Wycombe train station offers connections, and local bus services can also help you get closer to your desired route. It's advisable to check specific route access details and public transport schedules beforehand.
Parking is generally available in and around Chepping Wycombe, particularly in town centers or designated car parks near popular starting points for routes. Many routes begin from areas like Gomm Valley or Penn, where local parking options can be found. Always check local signage for parking restrictions and fees.
Spring and autumn are often considered ideal for road cycling in Chepping Wycombe, offering pleasant temperatures and beautiful scenery as the Chiltern Hills change colors. Summer can also be excellent, though routes might be busier. Winter cycling is possible but requires appropriate gear for colder, potentially wetter conditions.
The Chiltern Hills region is dotted with picturesque villages and market towns, many of which offer charming cafes, traditional pubs, and local shops. While specific amenities vary by route, you'll often find opportunities to stop for refreshments, especially when passing through places like Penn Village or Old Amersham.


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