Day 1: Arrival in Monmouth.
Day 2: Monmouth to Grosmont - 14 miles (22 km)
Your walk begins by Monmouth's 700-year old stone bridge, one of a number of historic structures built during the town's medieval heyday. There are plenty more interesting buildings on today's 8-mile walk to Skenfrith, including a 5th century church build in honour of one of King Brychan's forty-nine children! There are some steeper inclines followed by a welcome descent into Skenfrith where the first of the “Trilateral Castles” is to be found - a quiet ruin surrounded by a perfect carpet of turf. A stroll around the unusual, stocky church at the centre of this small village is also recommended before you heading northwards (and upwards!) to the pretty village of Grosmont. Here the second castle of the day awaits. Built in the 11th century, the castle is well-preserved and the nearby church contains some beautiful stone carvings and is also worth a visit.
Day 3: Grosmont to Longtown - 11 miles (18 km)
Enjoy excellent views down to the Monnow during the first part of the day. The bulk of the Black Mountains to the northwest looms closer today, as you continue along the Monnow's course. Once the scene of violent battles between the Welsh and the English, the landscape is dotted with the remnants of medieval castles, bridges at strategic crossings and churches. There is evidence too of earlier occupation – the church at Oldcastle stands on the site of a Roman earthwork. At Longtown look out for a passage cut into the Black Mountains leading to Llanthony Priory! Evening provides a chance to quiz the locals about the legend over a pint of the local brew.
Day 4: Longtown to Hay on Wye - 15 miles (24 km)
A lovely walk today, with a mixture of farm paths and old drovers' roads. There are fine views of the Cat's Back and Hatterall Ridges above. Your route steers clear of these exposed uplands, happily remaining in the sheltered valley! You then emerge suddenly into a wide upland pasture beneath Hay Bluff, with the Wye Valley spread out below and the peaks of the Central Beacons visible twenty miles to the West. A perfect picnic spot with panoramic views! From here you join Offa's Dyke Path for a welcome descent to the “Town of Books” on the River Wye.