In this guide, we’ve reviewed our full collection of road biking routes around Chiltern to bring you the best rides in the region. To find the one which is right for you, click on any of the Tours to see a full breakdown of its details including elevation profiles and surface analyses, and browse real tips and photos shared by other members of the Komoot community.

Last updated: October 2, 2025

4.6

(5)

riders

1. Wending around Wendover - Chiltern Hills loop

78.7km

04:00

1,070m

Expert road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.

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Expert

4.3

(7)

riders

2. The Royal Standard pub loop - Chesham to Winchmore Hill

58.5km

02:40

460m

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

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Intermediate

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4.4

(8)

202

riders

3. Temperance Hall, Chesham loop from Chesham

38.6km

01:38

210m

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

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Easy

4.8

(12)

162

riders

4. Penn Common Pond – Penn Village loop from Gerrards Cross

29.6km

01:27

250m

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

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Easy

5.0

(3)

146

riders

5. Chiltern Velo Café – Temperance Hall, Chesham loop from Chalfont & Latimer

37.4km

01:41

240m

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

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Easy

5.0

(1)

108

riders

6. Aldbury Village Green and Pond – Ivinghoe Beacon Climb loop from Chesham

90.9km

04:08

840m

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

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Intermediate

4.7

(3)

107

riders

7. Temperance Hall, Chesham – Aston Hill Climb loop from Amersham

43.6km

01:58

420m

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

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Intermediate

5.0

(2)

110

riders

8. Winchmore Hill – Marlow Bridge loop from Great Missenden

65.0km

03:04

630m

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

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Intermediate

5.0

(2)

107

riders

9. Aldbury Village Green and Pond – Temperance Hall, Chesham loop from Chesham

48.7km

02:22

500m

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

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Intermediate

4.0

(2)

riders

10. Marlow Bridge – Climb to Cookham Dean loop from Seer Green and Jordans

44.2km

01:56

350m

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

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Intermediate

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Didn’t find what you were looking for?

Check out more Road cycling routes throughout Chiltern below and find the perfect route in your destination.

Seer Green Cholesbury-Cum-St Leonards Chesham Bois Coleshill Great Missenden Chartridge Chalfont St Peter Little Chalfont Little Missenden Amersham Chalfont St Giles Ashley Green The Lee Latimer And Ley Hill Penn Philipshill Wood Chesham Hodgemoor Wood Chenies

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Browse the best Road cycling routes in other regions.

Thames Wycombe Aylesbury Vale Chilterns Aonb South Bucks

The best road cycling routes around Chiltern

1. Wending around Wendover - Chiltern Hills loop

2. The Royal Standard pub loop - Chesham to Winchmore Hill

3. Temperance Hall, Chesham loop from Chesham

4. Penn Common Pond – Penn Village loop from Gerrards Cross

5. Chiltern Velo Café – Temperance Hall, Chesham loop from Chalfont & Latimer

6. Aldbury Village Green and Pond – Ivinghoe Beacon Climb loop from Chesham

7. Temperance Hall, Chesham – Aston Hill Climb loop from Amersham

8. Winchmore Hill – Marlow Bridge loop from Great Missenden

9. Aldbury Village Green and Pond – Temperance Hall, Chesham loop from Chesham

10. Marlow Bridge – Climb to Cookham Dean loop from Seer Green and Jordans

Other adventures around Chiltern

Most popular routes around Chiltern

Most popular attractions around Chiltern

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