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Chiltern

Chiltern

The best road cycling routes around Chiltern

4.6

(133)

5,499

riders

269

rides

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: December 12, 2025

4.7

(6)

riders

1. Wending around Wendover - Chiltern Hills loop

78.7km

04:00

1,070m

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

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Hard

4.3

(7)

riders

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

58.5km

02:40

460m

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

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Moderate

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4.5

(10)

194

riders

3. Temperance Hall, Chesham – A Little Street Kitchen loop from Chesham

38.7km

01:38

210m

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

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Easy

4.7

(15)

163

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

(1)

109

riders

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

90.9km

04:07

840m

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

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Moderate

5.0

(2)

117

riders

6. Winchmore Hill – Marlow Bridge loop from Great Missenden

65.0km

03:04

630m

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

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Moderate

4.7

(3)

105

riders

7. Temperance Hall, Chesham – Chiltern Velo Café loop from Amersham

43.6km

01:58

420m

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

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Moderate

5.0

(2)

101

riders

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

48.5km

02:21

500m

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

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Moderate

100

riders

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

44.3km

01:56

350m

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

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Moderate

3.0

(1)

riders

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

68.1km

03:17

750m

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

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Moderate

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

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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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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 – A Little Street Kitchen loop from Chesham

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

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

6. Winchmore Hill – Marlow Bridge loop from Great Missenden

7. Temperance Hall, Chesham – Chiltern Velo Café loop from Amersham

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

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

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

Other adventures around Chiltern

Most popular routes around Chiltern

Most popular attractions around Chiltern

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