Running around Chiltern is one of the best ways to explore more of this region. To help you discover the most beautiful places to run, we’ve reviewed our full collection of routes around Chiltern—and are proud to present the best running trails. Click on any of the routes for more details and browse real tips and photos uploaded by other runners.

Last updated: September 27, 2025

runners

1. Tyler's Hill and River Chess loop from Chesham — Chiltern Hills

8.28km

00:56

100m

Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

Navigate

Send to Phone

Save

Intermediate

runners

2. Penn Wood and Winchmore Hill loop from Common Wood Lane — Chiltern Hills

8.78km

00:56

100m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

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 in England and beyond.

116

runners

3. Hebert's Hole loop from South Heath

11.1km

01:12

130m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

4.0

(1)

runners

4. Hebert's Hole – Chesham Clock Tower loop from Amersham

46.7km

05:18

520m

Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Expert

runners

5. Running loop from Penn

7.71km

00:48

60m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

5.0

(1)

runners

6. Penn Wood loop from Penn Street

10.8km

01:11

90m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

7. West Wood – Walk Wood loop from Little Chalfont

11.4km

01:21

150m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

8. Chesham Clock Tower loop from Chesham

7.72km

00:49

80m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

4.0

(1)

runners

9. West Wood loop from Little Chalfont

5.89km

00:41

70m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

runners

10. Shardeloes Lake loop from Little Missenden

7.93km

00:54

80m

Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Navigate

Send to Phone

Save

Intermediate

Get access to more routes and recommendations from other explorers.

Already have an account?

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

Other adventures around Chiltern

Hike some of the prettiest scenery in England — Chiltern Way

Hiking Collection by

Alan

Beautiful hills far and wide – ride the Chilterns Cycleway

Cycling Collection by

Snapshooter46 (CC BY-NC-SA 2.0)

Ride six counties and the M25 – London Revolution loop

Road Cycling Collection by

Bhobo Zus

Unforgettable trails – serene wilderness in the Chiltern Hills

Hiking Collection by

Nature Kicks

Chilterns heritage routes — road and off-road rides in the Chiltern Hills

Cycling Collection by

WoolyMatt

Most popular routes around Chiltern

Hiking around Chiltern

Easy hikes around Chiltern

Road Cycling Routes around Chiltern

Cycling around Chiltern

MTB Trails around Chiltern

Waterfall hikes around Chiltern

Gravel biking around Chiltern

Most popular attractions around Chiltern

Places to see

Get inspired with the komoot mobile app

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

Join komoot Now

Didn’t find what you were looking for?

Check out more Running Trails & 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

Explore more

Browse the best Running Trails & Routes in other regions.

Thames Chilterns Aonb Aylesbury Vale Wycombe South Bucks

The best running trails around Chiltern

1. Tyler's Hill and River Chess loop from Chesham — Chiltern Hills

2. Penn Wood and Winchmore Hill loop from Common Wood Lane — Chiltern Hills

3. Hebert's Hole loop from South Heath

4. Hebert's Hole – Chesham Clock Tower loop from Amersham

5. Running loop from Penn

6. Penn Wood loop from Penn Street

7. West Wood – Walk Wood loop from Little Chalfont

8. Chesham Clock Tower loop from Chesham

9. West Wood loop from Little Chalfont

10. Shardeloes Lake loop from Little Missenden

Other adventures around Chiltern

Most popular routes around Chiltern

Most popular attractions around Chiltern

Get inspired with the komoot mobile app

Didn’t find what you were looking for?

Explore more

Get ready to conquer new peaks

We value your privacy ⛰️

We value your privacy ⛰️