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.

Tyler's Hill and River Chess loop from Chesham — Chiltern Hills	Intermediate 00:56 8.28km
Penn Wood and Winchmore Hill loop from Common Wood Lane — Chiltern Hills	Intermediate 00:56 8.78km
Hebert's Hole loop from South Heath	Intermediate 01:12 11.1km
Hebert's Hole – Chesham Clock Tower loop from Amersham	Expert 05:18 46.7km
Running loop from Penn	Intermediate 00:48 7.71km
Penn Wood loop from Penn Street	Intermediate 01:11 10.8km
West Wood – Walk Wood loop from Little Chalfont	Intermediate 01:21 11.4km
Chesham Clock Tower loop from Chesham	Intermediate 00:49 7.72km
West Wood loop from Little Chalfont	Intermediate 00:41 5.89km

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Map data © OpenStreetMap contributors
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1
Tyler's Hill and River Chess loop from Chesham — Chiltern Hills
00:56
8.28km
6:43/km
100m
110m
Intermediate
8
Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.
Map data © OpenStreetMap contributors
2
2
Penn Wood and Winchmore Hill loop from Common Wood Lane — Chiltern Hills
00:56
8.78km
6:22/km
100m
100m
Intermediate
5
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Map data © OpenStreetMap contributors
3
3
Hebert's Hole loop from South Heath
01:12
11.1km
6:27/km
130m
130m
Intermediate
116
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
4
4
Hebert's Hole – Chesham Clock Tower loop from Amersham
05:18
46.7km
6:48/km
520m
520m
Expert
4.0
(1)
60
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
5
5
Running loop from Penn
00:48
7.71km
6:15/km
60m
60m
Intermediate
56
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
6
6
Penn Wood loop from Penn Street
01:11
10.8km
6:35/km
90m
90m
Intermediate
5.0
(1)
54
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
7
7
West Wood – Walk Wood loop from Little Chalfont
01:21
11.4km
7:04/km
150m
150m
Intermediate
31
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
8
8
Chesham Clock Tower loop from Chesham
00:49
7.72km
6:18/km
80m
80m
Intermediate
34
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
Map data © OpenStreetMap contributors
9
9
West Wood loop from Little Chalfont
00:41
5.89km
6:57/km
70m
70m
Intermediate
4.0
(1)
30
Intermediate run. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Map data © OpenStreetMap contributors

Shardeloes Lake loop from Little Missenden

00:54

7.93km

6:46/km

80m

Intermediate

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

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Last updated:

September 8, 2025

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The best running trails around Chiltern

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

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

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Hebert's Hole loop from South Heath

Hebert's Hole – Chesham Clock Tower loop from Amersham

Running loop from Penn

Penn Wood loop from Penn Street

West Wood – Walk Wood loop from Little Chalfont

Chesham Clock Tower loop from Chesham

West Wood loop from Little Chalfont