4.6
(293)
12,002
riders
344
rides
Road cycling routes around Chesham Bois are set within the Chilterns National Landscape, characterized by rolling hills, ancient woodlands, and chalk streams. The area offers a diverse terrain with both challenging climbs and scenic descents across its distinctive chalk hills and lush countryside. An extensive network of country lanes provides numerous possibilities for road cyclists to explore the region. The River Chess also meanders through the area, contributing to the tranquil scenery.
Last updated: July 1, 2026
4.7
(9)
56
riders
78.7km
04:00
1,070m
1,070m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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.

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4.5
(11)
193
riders
38.8km
01:39
210m
210m
Easy road ride. Great for any fitness level. 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.
4.7
(3)
99
riders
43.6km
01:58
420m
420m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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Stop at No2 Pound Street (adjacent to the mini roundabout up the hill) Their main business is a delicatessen specialising in cheese and wine ... but you can grab a tea/cofffee with cake or a toastie, Sit outside or in depending on the weather! Highly recommended. If you've room in your saddlebag, grab a bottle of wine, with some excellent cheese, having taken note of the expert advice from the staff!
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Best cycling cafe in the area. Great views and coffee.
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Pace yourself and keep something back for the near 15% gradient section. Gentle finish.
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The walk starts out from Amersham town centre. Highly recommended for breakfast before starting the hike is Sycamore, my personal favourite place for breakfast in Amersham with a variety of food options and excellent coffee (make sure to try the Figgy Anzac cookies!). Other good options are Nena Craft Bakery and A Little Street Kitchen which are both nearby.
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Amazing pub, with an amazing history and even more beautiful walks around like Coleshill and Penn.
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In the summer there are tours for Β£3 donation from 2pm on Sunday
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The Chesham Bois area, nestled within the Chilterns National Landscape, features a diverse terrain of rolling hills, ancient woodlands, and valleys. You'll encounter both challenging climbs and scenic descents across its distinctive chalk hills and lush countryside. The region is known for its extensive network of country lanes, offering varied surfaces suitable for road cycling.
There are over 340 road cycling routes available around Chesham Bois, catering to a wide range of abilities. This includes approximately 150 easy routes, 160 moderate routes, and 30 more challenging options.
Yes, Chesham Bois is well-connected to significant cycling networks. Sections of the 273km (170-mile) circular Chilterns Cycleway, specifically parts of its Central Loop, pass through the area. Additionally, National Cycle Route 57, a 101km (63-mile) Sustrans route connecting the Cotswolds to Welwyn Garden City, also goes through Chesham.
The area offers several points of interest. You can cycle past the tranquil Stocker's Lock and Stone Bridge, or the picturesque River Chess Stepping Stones and Weir. Other notable sites include Old Amersham Town Centre and the historic Hawridge Windmill. For more natural history, consider exploring Cholesbury Camp Iron Age Hill Fort or Chipperfield Common Woodland and Ponds.
Absolutely. Chesham Bois offers around 150 easy road cycling routes. A good option for a relaxed ride is the Temperance Hall, Chesham β A Little Street Kitchen loop from Chesham, which is 24.0 miles (38.7 km) and leads through rolling countryside.
Many charming hilltop villages like Cholesbury, Hawridge, Ley Hill, Ashley Green, Latimer, and Chenies offer welcoming pubs and cafes. The Chiltern Velo CafΓ© & Bike Workshop in Hawridge is a popular stop specifically for cyclists, providing a cafΓ©, outdoor terrace, and bike servicing. You can find it along routes such as the Temperance Hall, Chesham β Chiltern Velo CafΓ© loop from Amersham.
The area is highly rated by the komoot community, with an average score of 4.6 stars from over 240 reviews. Cyclists often praise the varied terrain, from challenging climbs to scenic descents, and the extensive network of country lanes that offer limitless possibilities for exploration within the beautiful Chilterns National Landscape.
Non-folding bicycles can be transported on the Metropolitan line outside of peak times, making it convenient to reach Chesham Bois and start your cycling adventures directly from the station.
Yes, many of the routes in Chesham Bois are circular, allowing you to start and end your ride in the same location. For example, the Wending around Wendover - Chiltern Hills loop and the The Royal Standard pub loop - Chesham to Winchmore Hill are both popular circular options.
The Chilterns National Landscape is beautiful year-round, but spring and autumn offer particularly pleasant conditions with mild temperatures and vibrant scenery. Summer is also excellent, though routes can be busier. While mostly paved, some sections of the Chilterns Cycleway can become rutted and muddy in wetter conditions, so consider this for winter rides.
Yes, the rolling hills of the Chilterns provide plenty of challenging climbs. The Wending around Wendover - Chiltern Hills loop is a difficult 48.9-mile (78.7 km) route with over 1000 meters of elevation gain. Another route, the Aldbury Village Pond β Ivinghoe Beacon Climb loop from Chesham, includes a notable climb towards Ivinghoe Beacon.


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