Embark on a challenging 5-day, 76-mile circular trek starting and ending at the historic town of Chepstow. Straddling the scenic borderlands of England and Wales, this route immerses you in the tranquil ancient woodlands of the Forest of Dean, the dramatic river bends of the Wye Valley, and rolling Monmouthshire countryside.
Along the way, you’ll encounter rich wildlife—from soaring red kites to wild boar—alongside panoramic viewpoints like Symonds Yat and sweeping vistas stretching toward the Brecon Beacons. Steep climbs and rugged, overgrown footpaths keep the journey demanding, but the effort is rewarded each evening with peaceful campsites and iconic historic landmarks, including Goodrich Castle, Skenfrith Castle, and the haunting ruins of Tintern Abbey.
A late start due to train problems, a simple 2.5 hr direct route became 4 trains and nearly 6.5 hrs! From the station at Chepstow you climb through the town and steeply up onto the Gloucestershire way passing farmers fields, pretty woodland paths and quiet country lanes. Stunning views over the Severn estuary and its famous bridge on one side and forests and hidden valleys on the other. After much uphill, down hill, up hill, down hill some more you get to one last super steep climb to campsite 1.
Campsite: https://www.fodglampandcamp.co.uk/
A day of gently gradients but a LONG way! Mostly within the forest today you drift off into a wooded trail of tranquillity, Ive seen red kites, deer, common lizards and even a family of wild boar as I amble along. Eventually though you reach the other side and drop down to walk along the River Wye towards Goodrich and its impressive castle (English Heritage). A couple of uphill miles from Goodrich Village you reach your camp for the night and a much needed rest.
Campsite: https://elmsdalecamping.co.uk/
Another long one today starting with some farm tracks and river paths, this is however easier said than done! Sadly (as it is beautiful) the North Wye valley has proven to be some of the worst signed and maintained footpaths I have ever seen, waist high nettles/brambles, trees down completely blocking routes, broken stiles and bridges, no signage for miles. Anyway, you soon start your climb up towards Symonds Yat and its famous viewpoint (slight diversion off route if you want to see this) before dropping down to the pubs either side of the river. This is the start of many miles of gravel track following the route of an old railway next to the river heading towards Monmouth. A long slog of beautiful but very undulating farmland then winds you slowly up to Skenfrith with its Castle (CADW), pretty church and shortly your next rest spot.
Campsite: https://www.threecastlescaravanpark.co.uk/
Heading away from Skenfrith you cross farmers fields, wooded creeks and quiet country lanes. Sadly this area is yet again a display of how bad footpaths can be maintained, have adjusted my original route to account for this! This beautiful area with its rolling hills has endless views towards Monmouth and the Wye valley on one side and the Brecon Beacons on the other. Dropping sharply down you cross a bridge over the main A40 dual carriage way, quite a shock after so many miles of tiny lanes. At this point the route gets much much harder! A steep gravel path leads you onto a steeper one across farmers fields then onto an even steeper on through some woods, definitely a thigh (and everything else burner!) Thankfully you eventually reach the top and follow some pleasant lanes and footpaths to the next campsite.
Campsite: https://highlandsholidaysmonmouth.com/campsite/
Passing through some stunning woodland you quickly head down and join the Offa’s Dyke path crossing fields and through woodlands whilst winding along next to the river. After some miles you will reach the little village of Tintern where you can find country pubs, coffee shops and lots of local history including its stunning Abbey ruins (CADW). If you wanted you can get the bus back to Chepstow from here or climb up through the woods onto the overlooking hills that roll you back to the finish point and train home. If you have time before heading home its well worth visiting Chepstow castle (CADW), situated on a small escarpment to one side of the town you get great views and dramatic ruins to finish off your walk (about 15 mins from Station).