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United Kingdom
Wales
South Wales
Monmouthshire

Chepstow

The best cycling routes around Chepstow

4.7

(44)

644

riders

39

rides

Touring cycling routes around Chepstow offer diverse landscapes, from the banks of the River Wye to the Severn Estuary. The area is characterized by varied terrain, including wooded valleys, rolling hills, and riverside paths within the Wye Valley National Landscape. Cyclists can find routes that explore historical landmarks and natural features, providing a range of experiences.

Best touring cycling routes around Chepstow

  • The most popular touring cycling route is Caldicot and Shirenewton loop from Chepstow, a 24.9 miles (40.1…

Last updated: May 1, 2026

5.0

(1)

7

riders

#1.

Caldicot and Shirenewton loop from Chepstow

40.1km

02:31

400m

400m

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

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Moderate

Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard
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Hard bike ride. Very good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Hard

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate

Moderate bike ride. Good fitness required. Mostly paved surfaces. Suitable for all skill levels.

Moderate
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Popular around Chepstow

GB Divide — Great Britain end to end off-road on GBDURO

Land's End to John O'Groats – an unforgettable ride

Bath to Chepstow – a family cargo bike trip into Wales

Wye Valley Walk — A riverside hike from lowlands to mountains

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GB Divide — Great Britain end to end off-road on GBDURO

Cycling Collection by

The Racing Collective

Tips from the Community

Klaske Schep
April 15, 2026, Tidenham Tunnel

Tidenham Tunnel opening hours 1 April -30 April 8am-6pm 1 May - 15 Aug 7am-7pm 16 Aug - 30 Sept 8am-6pm 1 Oct - 31 March Tunnel closed

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A nice way to get to Chepstow without the traffic.

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What a gem this place is. Homemade food, great staff, a warm welcome and very popular with lovely views of the canal

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Great for coffee, tea and cakes 😍

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We were a team of six doing the LEJOG and this was a great stop for us. Very bike friendly with great food.

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Stunning views on a clear day and the gateway to some great cycling in Bristol, Bath and beyond.

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Some great views of Tintern from this viewpoint

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This was a lovely place on a sunny day to watch the world go by

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Frequently Asked Questions

How many touring cycling routes are available around Chepstow?

There are over 40 touring cycling routes around Chepstow, offering a wide range of options for different skill levels and preferences. These routes explore the diverse landscapes of the Wye Valley National Landscape and the Severn Estuary.

What kind of terrain can I expect on touring cycling routes near Chepstow?

The terrain around Chepstow is varied, featuring wooded valleys, rolling hills, and tranquil riverside paths along the River Wye. You'll find routes with significant elevation gains, such as the challenging 'The Tumble' climb, as well as more relaxed, flatter sections, including multi-use off-road paths like the Wye Valley Greenway.

What do other touring cyclists say about the routes in Chepstow?

The touring cycling routes in Chepstow are highly rated by the komoot community, with an average score of 4.7 stars from over 50 reviews. Cyclists often praise the scenic views, varied terrain, and the opportunity to explore historical landmarks and natural features.

Are there easy touring cycling routes suitable for beginners in Chepstow?

Yes, Chepstow offers easy touring cycling routes suitable for beginners. For a relaxed experience, consider the new five-mile multi-use off-road Wye Valley Greenway, which connects Chepstow with Tintern along a disused railway. There are 2 easy routes in the area, providing gentle options for those new to touring cycling.

Are there any circular touring cycling routes around Chepstow?

Yes, many touring cycling routes around Chepstow are circular, allowing you to start and finish in the same location. An example is the Caldicot and Shirenewton loop from Chepstow, a moderate 24.9-mile route exploring the Monmouthshire countryside.

What historical landmarks and natural features can I see along the touring cycling routes?

Touring cycling routes around Chepstow offer access to numerous historical landmarks and natural features. You can visit the dramatic Chepstow Castle, the romantic ruins of Tintern Abbey, and the historic Tintern Wireworks Bridge. Natural highlights include the Giant's Cave in the Wye Valley and stunning views of the River Severn.

Are there any particularly scenic touring cycling routes with great viewpoints?

Absolutely. Many routes offer spectacular views. The Monmouth and Tintern loop from Chepstow – Wye Valley provides challenging climbs with rewarding scenic vistas through the Wye Valley. You can also find panoramic views over the Bristol Channel, Black Mountains, and Brecon Beacons from Chepstow Park Wood, and the Devil's Pulpit offers fantastic views over Tintern Abbey.

Are there any long-distance national cycle routes accessible from Chepstow?

Yes, Chepstow serves as a starting point for two significant long-distance routes: the Celtic Trail, which spans 220 miles across the southern edge of Wales, and Lon Las Cymru, an 185-mile journey north through the Brecon Beacons to Snowdonia. These routes offer extensive touring opportunities for experienced cyclists.

What is the best season for touring cycling in Chepstow?

Chepstow is enjoyable for touring cycling throughout much of the year. Spring and autumn offer pleasant temperatures and beautiful scenery, with changing foliage in the Wye Valley. Summer provides longer daylight hours, while milder winter days can also be suitable, though some unpaved sections might be muddier. Always check local weather forecasts before heading out.

Are there family-friendly touring cycling options in Chepstow?

Yes, Chepstow offers family-friendly cycling options, particularly along the Wye Valley Greenway, a multi-use off-road path that is safe and scenic for all ages. This route connects Chepstow with Tintern and runs through the impressive 1km Tidenham tunnel, providing an engaging experience for families.

Where can I find parking for touring cycling routes in Chepstow?

Chepstow has various parking options available for visitors. Many routes start directly from the town, where public car parks can be found. For specific route starting points, it's advisable to check the route details on komoot, as some may have designated parking areas nearby.

Can I combine touring cycling with public transport in Chepstow?

Chepstow is well-connected by public transport, including train services, which can be useful for combining with touring cycling. This allows for one-way rides or accessing routes further afield. Always check train operator policies regarding bicycles before planning your journey.

Are there cafes and pubs along the touring cycling routes for refreshments?

Yes, the Chepstow area, particularly along popular routes like those heading towards Tintern and Monmouth, offers various cafes and pubs where you can stop for refreshments. These establishments provide opportunities to refuel and enjoy local hospitality amidst your ride.

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