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United Kingdom
Wales
South Wales
Newport

Caerleon to Monmouth loop via Usk

Hard

4.0

(1)

19

riders

Caerleon to Monmouth loop via Usk

03:42

72.4km

990m

Road cycling

This difficult 45.0-mile (72.4 km) road cycling loop from Caerleon to Monmouth via Usk offers challenging climbs and scenic Wye Valley views

Last updated: February 26, 2026

Tips

Your route passes through protected areas

Please check local regulations for:

Wye Valley AONB

Waypoints

A

Start point

Parking

Get Directions

1

663 m

Coffiology

Highlight • Cafe

Good coffee and cakes!

Tip by

2

13.0 km

Usk Bridge

Highlight • Monument

The old red sandstone bridge was built between 1746 and 1747. It has five arches and was widened in 1836-7, although it might not feel like it if traffic is busy! If you opt for the footpath, please dismount.

Tip by

3

33.8 km

Monnow Bridge and Gatehouse

Highlight • Bridge

Sometimes referred to as Monmouth Bridge, Monnow Bridge is a charming medieval stone gated crossing, the last fortified river bridge in Britain. Once, this kind of crossing was a common …

Tip by

4

47.8 km

Tree-Lined Road Towards Devauden

Highlight (Segment) • Viewpoint

Resurfaced road a smooth rolling strip of tarmac through the forest. It's beautiful in autumn with all the colours or amazing in spring as the forest starts to grow again!

Tip by

5

62.6 km

Parc Seymour Official Climb

Highlight • Climb

Nice climb, one of the Official Welsh climbs

Tip by

B

72.4 km

End point

Parking

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Way Types & Surfaces

Way Types

68.8 km

2.27 km

1.34 km

< 100 m

Surfaces

50.8 km

21.7 km

< 100 m

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Elevation

Elevation

Nothing selected – click and drag below to see the stats for a specific part of the route.

Highest point (290 m)

Lowest point (10 m)

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Weather

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Tuesday 5 May

14°C

7°C

-- %

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This route was planned by komoot.

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Frequently Asked Questions

Is the Caerleon to Monmouth loop suitable for beginner cyclists?

This route is classified as difficult and is best suited for experienced road cyclists with a good level of fitness. It features significant elevation gain, including hilly sections and steep climbs, such as the Parc Seymour Official Climb. Some segments might even be unpaved and difficult, requiring cyclists to push their bikes.

What is the terrain like on this road cycling route?

The route primarily follows mostly well-paved surfaces and quiet roads. However, be prepared for challenging sections with steep gradients and hilly roads. While much of it is tarmac, some parts, particularly between Cwmbran and Monmouth, can be unpaved and difficult, making it a demanding ride.

Where can I park to start the Caerleon to Monmouth loop?

You can typically find parking in Caerleon, which is the starting point for this loop. Look for public car parks within the town. Alternatively, parking options are also available in Usk and Monmouth if you prefer to start your ride from one of those locations.

What are the main points of interest along the Caerleon to Monmouth loop?

The route is rich in both natural beauty and historical sites. You'll pass through charming villages and enjoy stunning scenery in the Wye Valley. Notable highlights include the Roman Amphitheatre in Caerleon, the historic Usk Bridge, and the unique medieval Monnow Bridge and Gatehouse in Monmouth. You'll also find scenic viewpoints like the Tree-Lined Road Towards Devauden.

What is the best time of year to cycle this route?

The best time to cycle the Caerleon to Monmouth loop is generally during the spring, summer, and early autumn months (April to October). During these periods, you can expect more favorable weather conditions, longer daylight hours, and the full beauty of the Wye Valley. Winter cycling can be challenging due to colder temperatures, shorter days, and potentially wet or icy road conditions.

Are there any cafes or refreshment stops along the way?

Yes, the route passes through several towns and villages where you can find refreshment stops. Usk and Raglan offer various shops and pubs. In Monmouth, you'll find options like Coffiology, a popular cafe. It's always a good idea to carry some snacks and water, especially on longer stretches between towns.

Does the route intersect with other well-known cycling or walking paths?

Yes, this route incorporates sections of several other paths. You will find yourself on parts of the National Cycle Network Route 42, which includes the car-free Peregrine Path. Other intersecting trails include EuroVelo 2 - Capitals Route - part United Kingdom 2, Usk Valley Walk, and Monnow Valley Walk, among others.

Is the Caerleon to Monmouth loop dog-friendly?

As this is primarily a road cycling route, it is generally not suitable for cycling with dogs, especially given the challenging terrain and potential for traffic on some sections. If you are looking for dog-friendly activities in the area, consider walking trails where dogs are permitted, usually on a leash.

Do I need any permits or pay entrance fees to cycle in the Wye Valley National Landscape?

No, there are no specific permits or entrance fees required to cycle this route through the Wye Valley National Landscape. The roads and public paths are freely accessible. However, always respect private property and follow the Countryside Code.

What kind of views can I expect along the route?

You can expect stunning and varied views throughout the ride. The route offers gorgeous views over the River Usk, expansive vistas over Monmouthshire, and the picturesque scenery of the Wye Valley at every turn. On clear days, you might even catch glimpses of the distant Brecon Beacons.

What should I bring for this challenging road cycling trip?

Given the route's difficulty and length, it's essential to be well-prepared. Bring a well-maintained race bike, appropriate cycling attire, a helmet, plenty of water, energy snacks, a repair kit (spare inner tubes, pump, levers), and a first-aid kit. A GPS device or a printed map of the route is highly recommended, as is a fully charged phone for emergencies.

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