Chepstow is a historic town situated on the Welsh-English border, offering a diverse landscape ideal for outdoor activities. The region is characterized by the Wye Valley National Landscape, with its ancient woodlands and riverbanks, and the adjacent Forest of Dean, known for its extensive network of paths. The River Wye and views of the River Severn estuary further define the area's natural features, making it suitable for several sports like road cycling, hiking, jogging, touring cycling, mountain biking, and gravel…
104
Routes
4.5
(268)
Average rating
3087
People visited

4.6
(48)
242
hikers
21.2km
06:14
590m
590m
Hard hike. Very good fitness required. Mostly accessible paths. Sure-footedness required.

4.6
(29)
171
hikers
15.8km
04:31
370m
370m
Moderate hike. Good fitness required. Easily-accessible paths. Suitable for all skill levels.

4.0
(32)
145
hikers
6.25km
01:45
120m
120m
Moderate hike. Great for any fitness level. Mostly accessible paths. Sure-footedness required.

4.4
(18)
98
hikers
19.9km
05:40
440m
440m
Hard hike. Very good fitness required. Easily-accessible paths. Suitable for all skill levels.
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4.8
(5)
257
runners
19.7km
02:19
510m
510m
Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

4.0
(2)
58
runners
11.8km
01:24
310m
310m
Hard run. Very good fitness required. Mostly accessible paths. Some sure footedness required.

5.0
(2)
36
runners
6.25km
00:43
120m
120m
Moderate run. Good fitness required. Mostly accessible paths. Some sure footedness required.

5.0
(1)
39
runners
18.4km
01:57
180m
180m
Hard run. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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1.0
(1)
57
riders
66.7km
03:14
880m
880m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.

3.0
(1)
12
riders
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.

9
riders
111km
05:44
1,780m
1,780m
Hard road ride. Very good fitness required. Mostly well-paved surfaces and easy to ride.

12
riders
54.0km
02:31
510m
520m
Moderate road ride. Good fitness required. Mostly well-paved surfaces and easy to ride.
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5
riders
63.5km
05:45
1,350m
1,350m
Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary.

7
riders
31.1km
02:27
580m
580m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.

5.0
(2)
5
riders
Hard mountain bike ride. Very good fitness required. Advanced riding skills necessary.

5.0
(1)
6
riders
19.1km
01:31
360m
360m
Moderate mountain bike ride. Good fitness required. Suitable for all skill levels.
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4
riders
58.4km
04:15
1,050m
1,060m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

6
riders
40.1km
02:31
400m
400m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.3
(7)
100
riders
127km
07:56
660m
660m
Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

4.8
(5)
83
riders
55.2km
03:15
280m
280m
Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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10
riders
24.2km
02:08
470m
480m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

5.0
(2)
4
riders
36.8km
02:45
680m
680m
Hard gravel ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

6
riders
28.1km
02:04
400m
400m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

2
riders
29.5km
02:06
440m
440m
Moderate gravel ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.
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Chepstow offers a diverse range of outdoor activities including Road cycling, Hiking, Jogging, Touring cycling, Mountain biking, and Gravel biking. The region features over 200 routes, with an average rating of 4.45 stars from more than 21,000 visitors.
Chepstow is a hub for road cycling, with 83 dedicated routes. These routes traverse the Wye Valley National Landscape and the Forest of Dean, offering diverse scenery and varying challenges. Explore options in the Road Cycling Routes around Chepstow guide.
Chepstow offers 38 hiking routes, including sections of the Wye Valley Walk and Offa's Dyke Path. Local trails like the Lancaut Peninsular Walk also provide scenic options. More details are available in the Hiking around Chepstow guide.
Chepstow offers family-friendly options, particularly the Wye Valley Greenway. This 5-mile (8 km) off-road path connects Sedbury and Chepstow to Tintern, providing a safe route for cyclists of all ages. The region also has specific routes tagged as family-friendly.
Chepstow is situated within the Wye Valley National Landscape and borders the Forest of Dean. Notable features include the River Wye, views of the River Severn estuary, and historical sites like Chepstow Castle and Tintern Abbey. The Tidenham Tunnel on the Wye Valley Greenway is also a unique point of interest.
Chepstow serves as a starting or finishing point for several long-distance trails. These include the Wye Valley Walk, the Offa's Dyke Path, and the Wales Coast Path. These trails offer extensive routes for hikers and walkers.
Chepstow provides 47 routes specifically for jogging. These trails offer varied terrain within the Wye Valley National Landscape and local areas. Consult the Running Trails around Chepstow guide for detailed options.
The Wye Valley Greenway is a 5-mile (8 km) off-road path connecting Sedbury and Chepstow to Tintern. It is suitable for cyclists of all ages and includes passage through the historic Tidenham Tunnel. This route offers a safe and scenic way to explore the area.
Komoot offers several guides for Chepstow, including Road Cycling Routes around Chepstow, Hiking around Chepstow, and Running Trails around Chepstow. Guides for general cycling, MTB, easy hikes, and gravel biking are also available.
Routes in Chepstow have an average rating of 4.45 out of 5 stars. This rating is based on feedback from more than 21,000 visitors who have explored the region's diverse outdoor paths.
Official information about Chepstow can be found on the Chepstow Town Council website. For direct inquiries, the Chepstow Town Council can be reached at +44 1291 626370.

