4.0
(1)
19
riders
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:
Waypoints
Start point
Parking
Get Directions
663 m
Highlight • Cafe
Tip by
13.0 km
Highlight • Monument
Tip by
33.8 km
Highlight • Bridge
Tip by
47.8 km
Highlight (Segment) • Viewpoint
Tip by
62.6 km
Highlight • Climb
Tip by
72.4 km
End point
Parking
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
Highest point (290 m)
Lowest point (10 m)
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Weather
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Tuesday 5 May
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7°C
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This route was planned by komoot.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.