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

Cholesbury-Cum-St Leonards

The best road cycling routes around Cholesbury-Cum-St Leonards

4.5

(257)

10,542

riders

523

rides

Road cycling around Cholesbury-Cum-St Leonards offers diverse landscapes within the Chiltern Hills Area of Outstanding Natural Beauty. The region is characterized by rolling hills, expansive ancient woodlands, open meadows, and distinctive chalk grasslands. Road cycling routes feature mostly paved surfaces with varying elevation gains, catering to different fitness levels. The topography includes numerous hills and scenic viewpoints across the Aylesbury Vale.

Best road cycling routes around Cholesbury-Cum-St Leonards

  • The most popular road cycling route is Temperance Hall, Chesham – A…

Last updated: July 14, 2026

5.0

(3)

156

riders

#1.

Ashridge House – Aldbury Village Pond loop from Northchurch

39.2km

01:57

380m

380m

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

Navigate with device

Send to Phone

Save

Moderate

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

Sign up for free

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

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

Easy
Sign up for free to see 519 more rides around Cholesbury-Cum-St Leonards.

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 Cholesbury-Cum-St Leonards

Unforgettable trails – serene wilderness in the Chiltern Hills

Hiking around Cholesbury-Cum-St Leonards

MTB Trails around Cholesbury-Cum-St Leonards

Gravel biking around Cholesbury-Cum-St Leonards

Running Trails around Cholesbury-Cum-St Leonards

Cycling around Cholesbury-Cum-St Leonards

Other adventures around Cholesbury-Cum-St Leonards

Unforgettable trails – serene wilderness in the Chiltern Hills

Hiking Collection by

Nature Kicks

Tips from the Community

John H
June 4, 2025, Kopp Lane Climb

This is a short tough climb which demands your full attention. Loved it.

0

0

Fabulous morning weekday ride.

0

1

Great Incline to the top

0

0

Beautiful forrest vibe lane. Makes you feel close to nature. Watch out for the potholes, especially if you don't have a photochromic lenses as it gets darks with tall trees around.

0

0

This was on my route unexpectedly. Left my mouth open for a bit. Very beautiful.

0

0

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.

1

0

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 (1843–1917), 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.

1

0

Jon Proctor
October 21, 2023, Ashridge House

Ashridge house and the surrounding woods are a great spot for a ride or a run. Elizabeth 1 spent parts of her childhood at the house.

1

0

Frequently Asked Questions

What kind of terrain can I expect on road cycling routes around Cholesbury-Cum-St Leonards?

The region, nestled within the Chiltern Hills, features diverse landscapes with rolling hills, expansive ancient woodlands, open meadows, and distinctive chalk grasslands. Routes primarily use paved surfaces, offering varying elevation gains from gentle gradients to significant climbs, catering to different fitness levels.

Are there road cycling routes suitable for beginners or those looking for an easy ride?

Yes, there are plenty of options for all skill levels. Over 200 easy road cycling routes are available. For example, the Temperance Hall, Chesham – A Little Street Kitchen loop from Chesham is an easy 24-mile route with gentle gradients, perfect for a relaxed ride.

Where can I find challenging road cycling routes with significant climbs?

For those seeking a challenge, the area offers routes with notable elevation gains. A popular moderate option is the Aldbury Village Pond – Ivinghoe Beacon Climb loop from Chesham, a 56.5-mile path that includes significant climbs and rewards cyclists with extensive views from Ivinghoe Beacon.

What scenic viewpoints or landmarks can I see while road cycling in the area?

The region is rich in scenic spots and historical landmarks. You can enjoy breathtaking panoramic vistas from Coombe Hill Viewpoint and Boer War Memorial, the highest point in the Chilterns. Ivinghoe Beacon also offers extensive views. Additionally, you might encounter the impressive Iron Age hillfort, Cholesbury Camp, or the prehistoric earthwork Grim's Ditch along various routes.

Are there any circular road cycling routes available?

Many of the road cycling routes in Cholesbury-Cum-St Leonards are designed as loops, allowing you to start and finish at the same point. For instance, the Aldbury Village Green and Pond – Temperance Hall, Chesham loop from Chesham is a 30.3-mile circular trail through varied terrain.

What is the best time of year for road cycling in Cholesbury-Cum-St Leonards?

The diverse landscapes, including ancient woodlands and open meadows, make spring and autumn particularly appealing for road cycling. Spring brings blooming wildflowers, while autumn offers vibrant foliage. Summer is also excellent, though routes can be more exposed to the sun. Always check local weather conditions before heading out.

Are there cafes or pubs along the road cycling routes for a stop?

Yes, the area is cyclist-friendly with establishments like the Chiltern Velo Café and Bike Workshop in nearby Hawridge. Many routes are designed to pass through villages or near local pubs, providing convenient stops for refreshments and meals. The region is known for routes often starting or finishing at local pubs.

What do other road cyclists say about the routes in Cholesbury-Cum-St Leonards?

The road cycling routes in Cholesbury-Cum-St Leonards are highly rated by the komoot community, with an average score of 4.5 stars from over 180 reviews. Cyclists often praise the varied terrain, scenic views, and the network of routes that cater to different ability levels.

Can I find road cycling routes that pass through ancient woodlands?

Absolutely. The region is rich in ancient woodlands, such as Captains Wood, areas along Kiln Lane, and Buckland, Pavis and Drayton Woods. The distinct Red Cedar Woods Path also offers a unique woodland cycling experience, providing shaded and picturesque sections for your ride.

Are there any road cycling routes that are particularly good for spotting wildlife or rare plants?

Yes, areas like Pitstone Hill and Coombe Hill are designated Sites of Special Scientific Interest (SSSI) due to their chalk grasslands, which are home to rare wildflowers, numerous butterfly species, and a variety of birdlife. Cycling through or near these areas offers opportunities for nature observation.

How long are the typical road cycling routes in this area?

Route lengths vary significantly to suit different preferences and fitness levels. You can find shorter loops around 24 miles, such as the Temperance Hall, Chesham – A Little Street Kitchen loop, up to longer rides like the The Lee Village Green – Bryants Bottom Road loop from Chesham which covers about 34.5 miles (55.5 km).

Most popular routes around Cholesbury-Cum-St Leonards

Hiking around Cholesbury-Cum-St Leonards

Most popular attractions around Cholesbury-Cum-St Leonards

Natural Monuments

Store rating

Get inspired with the komoot mobile app

With a 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.

ChartridgeChesham BoisPennColeshillAshley GreenAmershamCheshamChalfont St GilesGreat MissendenThe LeeHodgemoor WoodSeer GreenCheniesPhilipshill WoodLittle MissendenChalfont St PeterLittle ChalfontLatimer And Ley Hill

Nearby adventure guides

Things to Do around Chartridge

background

Get ready to conquer new peaks

Sign up for Free

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

© komoot GmbH

Privacy Policy