The best walks and hikes around Chepstow
4.4
(496)
3,245
hikers
38
hikes
Last updated: October 28, 2025
4.6
(41)
228
hikers
1. Tintern Abbey loop from Chepstow — Wye Valley
21.2km
06:14
590m
590m
Expert hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.
4.6
(25)
156
hikers
2. Chepstow Castle to Wyndcliff Wood — Wye Valley Way
15.8km
04:31
370m
370m
Intermediate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.
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4.0
(30)
134
hikers
3. Chepstow Castle & Wye River loop from Chepstow — Wye Valley
6.25km
01:45
120m
120m
Intermediate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.
4.4
(18)
92
hikers
4. To the Devil's Pulpit along the River Wye loop from Chepstow — Wye Valley
19.9km
05:40
440m
440m
Expert hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
4.9
(8)
77
hikers
5. Gloucester Hole – Chepstow Castle Entrance loop from Chepstow
10.9km
03:08
250m
250m
Intermediate hike. Good fitness required. Easily-accessible paths. 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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