Routes

Planner

Features

Updates

App

Login or Signup

Get the App

Login or Signup

Routes
Road cycling routes
United Kingdom
England
South East England
Buckinghamshire
Chiltern

Chesham Bois

The best road cycling routes around Chesham Bois

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.

Best road cycling routes around Chesham Bois

  • The…

Last updated: July 1, 2026

4.7

(9)

56

riders

#1.

Wending around Wendover - Chiltern Hills loop

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.

Navigate with device

Send to Phone

Save

Hard

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
guide_signup
Let us show you the way with the komoot mobile app
With aΒ free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

Sign up for free

Easy road ride. Great for any fitness level. Mostly well-paved surfaces and easy to ride.

Easy

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate

Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

Moderate
Sign up for free to see 340 more rides around Chesham Bois.

Get access to more routes and recommendations from other explorers.

Sign up for free

Already have an account?

Our route recommendations are based on thousands of hikes, rides, and runs completed by other people on komoot.

Start today with a free account

Your next adventure awaits.

Login or Signup

Popular around Chesham Bois

Chilterns heritage routes β€” road and off-road rides in the Chiltern Hills

Hiking around Chesham Bois

Cycling around Chesham Bois

Running Trails around Chesham Bois

MTB Trails around Chesham Bois

Gravel biking around Chesham Bois

Other adventures around Chesham Bois

Chilterns heritage routes β€” road and off-road rides in the Chiltern Hills

Cycling Collection by

foxy44

Tips from the Community

AliG
October 5, 2025, Wendover Village Centre

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!

0

0

Best cycling cafe in the area. Great views and coffee.

0

0

Pace yourself and keep something back for the near 15% gradient section. Gentle finish.

0

0

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.

0

0

Fabulous morning weekday ride.

0

1

Great Incline to the top

0

0

Amazing pub, with an amazing history and even more beautiful walks around like Coleshill and Penn.

0

0

In the summer there are tours for Β£3 donation from 2pm on Sunday

0

0

Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Chesham Bois?

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.

How many road cycling routes are available in Chesham Bois?

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.

Are there any long-distance or notable cycling routes that pass through Chesham Bois?

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.

What are some interesting landmarks or natural features to see while cycling in Chesham Bois?

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.

Are there any easy road cycling routes suitable for beginners or a more relaxed ride?

Absolutely. Chesham Bois offers around 150 easy road cycling routes. A good option for a relaxed ride is the Temperance Hall, Chesham – A Little Street Kitchen loop from Chesham, which is 24.0 miles (38.7 km) and leads through rolling countryside.

Where can cyclists find refreshments or bike services in the area?

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 – Chiltern Velo CafΓ© loop from Amersham.

What do other road cyclists enjoy most about cycling in Chesham Bois?

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.

How can I reach Chesham Bois with my bicycle using public transport?

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.

Are there any circular road cycling routes in Chesham Bois?

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.

What is the best time of year for road cycling in Chesham Bois?

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.

Are there routes with significant climbs for experienced road cyclists?

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 – Ivinghoe Beacon Climb loop from Chesham, includes a notable climb towards Ivinghoe Beacon.

Most popular routes around Chesham Bois

Hiking around Chesham Bois

Most popular attractions around Chesham Bois

Places to see

Store rating

Get inspired with the komoot mobile app

With aΒ free komoot account, you can easily find, customize, and navigate endless outdoor adventures.

or

Join komoot Now

Store rating

Explore more

Browse the best Road cycling routes in other regions.

ChartridgePennColeshillAmershamAshley GreenCheshamCholesbury-Cum-St LeonardsChalfont St GilesGreat MissendenHodgemoor WoodThe LeeSeer GreenCheniesPhilipshill WoodLittle MissendenChalfont St PeterLatimer And Ley HillLittle Chalfont

Nearby adventure guides

Things to Do around Chesham

background

Get ready to conquer new peaks

Sign up for Free

Explore
RoutesRoute plannerFeaturesHikesMTB TrailsRoad cycling routesBikepackingSitemap
Download the app
Follow Us on Socials

Β© komoot GmbH

Privacy Policy