4.7
(140)
5,414
riders
264
rides
Road cycling routes around Chiltern traverse an Area of Outstanding Natural Beauty characterized by rolling chalk hills, ancient beech woodlands, and dry valleys. The region offers varied terrain, including both gentle ascents and short, steep climbs typical of the UK. The River Thames also cuts through the southern end, adding riverine landscapes to the cycling experience. These features provide diverse settings for road cyclists.
Last updated: May 1, 2026
4.7
(6)
47
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)
34
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.
4.7
(15)
159
riders
29.7km
01:27
250m
250m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
5.0
(2)
128
riders
65.0km
03:04
630m
630m
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.
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.
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.
91
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
5.0
(7)
78
riders
37.7km
01:42
270m
270m
Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.
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Popular around Chiltern
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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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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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The Chilterns offer a wide variety of road cycling routes, with over 260 tours available on komoot. These routes cater to all skill levels, from easy loops to challenging climbs, ensuring there's something for every road cyclist.
Yes, the Chilterns provide numerous beginner-friendly road cycling options. You can find over 100 easy routes, many of which traverse the region's picturesque landscapes on quieter country lanes. An example is the Temperance Hall, Chesham – A Little Street Kitchen loop from Chesham, which is a moderate 24-mile ride.
Road cycling in the Chilterns is characterized by rolling chalk hills, ancient beech woodlands, and dry valleys. You'll encounter both gentle ascents and short, steep climbs typical of the UK. The River Thames also adds beautiful riverine landscapes to the southern end of the region, offering diverse and engaging terrain.
Absolutely. The Chilterns are known for their engaging inclines and challenging climbs. For instance, the Wending around Wendover - Chiltern Hills loop is a difficult 48.9-mile route with significant elevation gain, perfect for experienced cyclists seeking a demanding ride.
Yes, the Chilterns are home to several long-distance routes. The 170-mile Chilterns Cycleway is a major draw, primarily using well-maintained country lanes. For a challenging long-distance option, consider the Aldbury Village Pond – Ivinghoe Beacon Climb loop from Chesham, which spans over 56 miles (90 km).
The Chilterns offer many points of interest. You might pass by historic sites like the Cholesbury Camp Iron Age Hill Fort or natural features such as Prestwood Local Nature Reserve. Charming towns like Old Amersham with its medieval High Street are also accessible, offering a glimpse into the region's rich history.
Yes, many road cycling routes in the Chilterns pass through charming villages and market towns where you can find cafes and pubs. For example, the The Royal Standard pub loop - Chesham to Winchmore Hill is named after a local pub, and the Temperance Hall, Chesham – Chiltern Velo Café loop from Amersham specifically mentions a cycling-friendly cafe.
The Chilterns are beautiful year-round, but spring and summer are particularly popular. Spring brings vibrant bluebells to the ancient beech woodlands, while summer offers pleasant temperatures for longer rides. Autumn also provides stunning foliage. The well-maintained country lanes are generally suitable for cycling across multiple seasons.
Yes, road cycling is possible in the Chilterns during winter, though conditions can vary. The paved country lanes are generally accessible, but it's advisable to check weather forecasts for ice or heavy rain. Many routes offer sheltered sections through woodlands, and the region's charming pubs provide warm stops.
The Chilterns are highly rated by the komoot community, with an average score of 4.6 stars from over 130 reviews. Cyclists often praise the diverse and picturesque landscapes, the engaging mix of rolling hills and challenging climbs, and the quiet country lanes that make for a rewarding ride through an Area of Outstanding Natural Beauty.
Yes, the River Thames cuts through the southern end of the Chilterns, adding dramatic and beautiful riverine landscapes to the cycling experience. Routes like the Winchmore Hill – Marlow Suspension Bridge loop from Great Missenden offer opportunities to cycle near the river and enjoy its scenic beauty.
Many routes in the Chilterns pass through charming historic towns and villages. For example, the Marlow Bridge – Cookham High Street loop from Seer Green and Jordans takes you through areas with rich history and picturesque settings, allowing you to explore local heritage during your ride.


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