Trying to find the best Monmouthshire trails? AllTrails has 48 great hiking trails, running trails, walking trails and more, with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers, and nature lovers like you. If you're looking for the best trails around Abergavenny, Chepstow or Monmouth, we've got you covered. Ready for some activity? There are 29 moderate trails in Monmouthshire ranging from 2.7 to 19.7 miles and from 36 to 2,683 feet above sea level. Start checking them out and you'll be out on the trail in no time!

walking

hiking

views

nature trips

river

bird watching

running

wild flowers

wildlife

forest

historic site

backpacking

Monmouthshire, Wales Map
VIEW FULL MAP

What a nightmare. It was given 5 stars. What a joke. A complete waste of time. It’s the worst walk I have ever been on. Bad directions. Avoid this walk.

hiking
16 days ago

Great hike or run. Lots of different paths and gradients. Chose your own, don’t let AllTrails dictate to you. Beaten tracks are for beaten men... or women! Panoramic views amazing at the top

This is a great trail. I did it clockwise starting at Chepstow (better for those using public transport from Bristol). It took about 6 hours including a break at Tinerton. This route meant I started with the gorgeous forest section and tackled the fields and B roads after lunch. I might try it anti-clockwise next time. Some steep climbs and gorgeous scenery--although it was really misty when I did it. Would definitely recommend.

hiking
private property
1 month ago

hiking
muddy
rocky
1 month ago

Great walk, although muddy and rocky in areas.

hiking
1 month ago

A pleasant walk with some lovely views and a few other things to look at along the way. White Castle is very underated and very picturesque. A quick diversion to examine the site of the old mill (at halfway) is worthwhile.

1 month ago

Good walk for all levels of fitness

1st time up the Sugar Loaf... checked the forecast first, all looked good for dry albeit slightly cloudy. travelled up to the main car park on Sugar Loaf, which was further up than expected. Swung on the backpack with waterproofs & drink (although weatherman said dry)... got the dogs out of the car and started on main pathway up to highest car park and then onto one of the main gassed &slightly muddy pathways which are obvious. this being a good job as no trail markers were evident to us. lots of people out today with family, friends and dogs (some off lead, although there were sheep around!). Within 15 mins into our walk the weatherman curse happened... it started to rain... only fine but plenty of it, soap quick stop for the waterproof jackets & pants. glad we put the dogs coats on too, as the wind picked up and while I have no idea of the wind chill factor, it was definitely something that could have spoilt the hike had we not had the right kit with us. Looks like we stayed mainly to one of the main routes as it was busy and when it came to ascending to the top, it wasn't as steep as some of the other routes. we got to the top where the cold was low (although we did get to see some of the views), the wind was cold and the stay at the top was a shirt one.... not long enough to stay for coffee but long enough to take a selfie of the dogs and the Sugar Loaf sign. By the time we made it back to the car park the weather hadn't changed much so all kit (including the dogs coats) were removed and left to dry in the car during the journey home. I've been meaning to do Sugar Loaf for a while now, so very pleased I did. maybe next time the weather will be nicer!

Great walking with amazing views from the ‘Lonely Shepherd’ at the very top (helped by a beautiful sunny day) and plenty of rivers and streams on route as well as the Devil’s bridge waterfall. Interesting and varied terrain and scenery. We unintentionally walked the route in reverse (out the far end of the car park) and did the main steep stretch first.. there are a couple of steep sections. The route at the top of the hill didn’t seem to follow the obvious paths and we did get lost.. recommend following the main paths and not the route map.

Lovely walk but be prepared for about 30/40 minutes of pretty hardcore hill climbing at the start. I'm not the fittest and kept hoping the next horizon would be kinder. It wasn't! Saying that, once it levelled out it was a satisfying walk. Very misty so we weren't able to fully appreciate the views but very nice overall Only wish it had been a clearer day!

Really nice walk. Unfortunately it was pretty foggy at the top so couldn’t take in the views. Would definitely come and do it again.

Very windy on the top but lovely views!

hiking
muddy
1 month ago

1 month ago

An OK route, but can noone here spell Skirrid correctly?

1 month ago

A great walk though you have to pay to park nowadays. A Spitfire crashed in the woods during WWII. It's called Skirrid, Skirrid Fawr (Big Skirrid) or even Holy Mountain. There's no "The".

How can't you love this route? For some good fun look at incorporating Tidenham tunnel into the route. It's about 1.5 miles long and the track has never been taken up.

The Wye is stunning, Monmouth bridge and Redbrook viaduct are amazing (parking is good here), the fabulous Incline (tram) bridge, the roundhouse, where Nelson visited, and the fantastic views from there are just some of the highlights. Personally I wouldn't walk down the road from the Kymin as there are good paths.

I do this walk and variations of it very regularly, so it takes me a lot less than two hours, but it is a strenuous walk if you're not used to the hills. I was lucky enough to get to know the totem pole sculptor Neil Gow a few years ago while he created this excellent piece on site. He is responsible for many excellent and very local carved sculptures. There's good parking in Redbrook of course if you want to start in England and you get to cross the lovely old railway viaduct across the Wye. The Boat Inn is good too. The Inn at Penallt is currently closed.

walking
muddy
scramble
2 months ago

This is a very enjoyable walk. It is very steep over rocks on the walk up to Devils Pulpit which can be muddy and slippery (this is not an easy walk in my opinion) however you are rewarded with stunning views, quiet trails and an easy walk back down. I will be making this a regular walk!

Nice fun valley trail. Follow wye valley walk from Tintern and Offas Dyke path from Chepstow. Not too muddy for winter run.

Lovely trail with some splendid views and a good choice of path routes. Highly recommend!

hiking
private property
3 months ago

This could be a lovely walk but a couple of areas have been made difficult to pass by private landowners. In addition, due to ancient rivers a lot of fields have been easily flooded or made very very muddy.

hiking
muddy
off trail
over grown
rocky
snow
3 months ago

Load More