The best running trails around Chepstow
4.7
(43)
1,021
runners
54
runs
Last updated: October 22, 2025
4.7
(3)
236
runners
1. Wye valley trail to Tintern from Chepstow
19.7km
02:19
510m
510m
Expert run. Very good fitness required. Mostly accessible paths. Some sure footedness required.
4.0
(2)
58
runners
2. Giants cave & Eagles Nest loop from Chepstow — Wye Valley
11.8km
01:24
310m
310m
Expert run. Very good fitness required. Mostly accessible paths. Some sure footedness required.
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5.0
(2)
33
runners
3. Chepstow Castle & Wye River loop from Chepstow — Wye Valley
6.25km
00:43
120m
120m
Intermediate run. Good fitness required. Mostly accessible paths. Some sure footedness required.
48
runners
4. Tidenham Tunnel – Chepstow Castle loop from Chepstow
16.9km
01:47
160m
160m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
34
runners
5. Chepstow Castle – Brockweir Bridge loop from Chepstow
38.1km
04:37
900m
900m
Expert run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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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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