The best road cycling routes around Chepstow
4.3
(52)
1,627
riders
84
rides
Last updated: November 10, 2025
1.0
(1)
46
riders
1. A loop of the Wye Valley, Tintern Abbey & Monmouth from Chepstow
65.8km
03:15
850m
850m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
3.0
(1)
12
riders
2. Gloucester & the River Severn loop from Chepstow
106km
05:07
1,060m
1,060m
Hard road ride. Very good fitness required. Some segments of this route may be unpaved and difficult to ride.
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20
riders
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
9
riders
4. Abergavenny and Y Tymbl from Chepstow loop — Wye Valley
111km
05:44
1,780m
1,780m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.
4.0
(2)
157
riders
5. View of the River Wye – Tintern Abbey loop from Chepstow
79.8km
03:36
820m
820m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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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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