The Trail Description by Chris Barber

(Updated 30th June 2011)

The village is named after a hill on its southern side (Le Gros Mont), which is better known today as the Graig. At one time Grosmont was the third largest town in the county. However, in 1405 it was reduced to the size of a village when Owain Glyndwr’s army paid a visit and destroyed a large number of buildings, which were never rebuilt.

Having parked on the roadside in the village. Head downhill and look out for the sign “Grosmont castle ancient monument” on your left. Follow the lane to reach a field. Carry straight on to reach the entrance to Grosmont Castle.

Eleanor was brought to England by William, bishop-elect of Valence, who immediately established great influence over King Henry III. Eleanor married King Henry in Canterbury Cathedral on January 4, 1236 and was crowned in Westminster Abbey sixteen days later. Henry was devoted to his beautiful young bride, who was just half his age and he gave her magnificent jewellery said to have cost £30,000, which was an enormous sum in those days.

It was thought that the royal couple often visited Grosmont for this castle was one of their favourite residences and they had it equipped with costly furniture and decorations for they both possessed a love of fine arts.

The castle overlooks the River Monnow and comprises a keep, curtain walls with angle towers, a massive gatehouse and is surrounded by a deep but dry moat. The original foundations of the castle date from 1070, but the main part of the building is 13th century.

A striking feature is a 13th Century chimney surmounted by a carved coronet, which rises above a large fireplace which was thought to have heated Eleanor’s private chamber. It is traditionally known as Eleanor’s Chimney.

Grosmont Castle is the scene of a dramatic episode involving Henry III. The King in 1233, in a fit of temper had declared that the Marcher Lords should forfeit their estates. He marched on the border of Wales with a motley army of foreign mercenaries and half-trained English, with the aim of enforcing his orders. He captured Grosmont town and castle, but the dispossessed Lords Marcher managed to persuade their old enemy, Prince Llewellyn to come to their aid. With a body of fierce Welshmen, they made a sudden attack early one misty morning on Henry’s rabble. The king’s troops panicked and fled down the Monnow valley. The story goes that they ran away clad in flimsy nightgowns, hotly pursued by mail clad Welshmen bristling with weapons.

After inspecting the castle ruins, return over the footbridge and follow the outside of the fence around to the right to view the exterior walls. Continue to reach two large trees (oak and ash) just inside the fence line at the rear of the castle. Turn away from the castle and cross the field to reach a stile by a field gate in the fence line ahead. Go over and head on towards a lone oak tree to the right of a dwelling. Go between the tree and the bungalow boundary wall, turn left to reach a wooden kissing gate. Go out onto the road and follow it up to the left.

By a junction on the left (Tollstone Way), look out for a small standing stone near the hedge. It has been suggested that this may have been a milestone.

Descend into the village to reach the old Town Hall near to a road junction down to your right.  

Visitors are often surprised to learn that Grosmont was once important enough to have a Mayor and a Corporation.

The mayor was always elected at the end of May or beginning of June each year. It was a straightforward procedure since the mayor appointed his personal ale taster, who usually was appointed mayor the following year. On the ground floor is a large stone, which is known as the ‘Toll Stone’. There was once a custom that the first woman to place her basket on this stone on market day would be allowed to trade free of toll. Another ancient stone can be seen on the side of the road opposite the Town Hall.

Descend the road to the right, passing the Town Hall and some public toilets on your left.

A gabled building on the right was once an inn called ‘The Old Duke of York’.

Look out for a narrow lane on the left. Follow this and shortly turn right through a metal kissing gate into the churchyard. Make your way to the entrance to the church.

The church is surprisingly large, giving an indication of the former importance of the town. Brian Wallingford, the second Lord of Abergavenny in about 1110, started its construction but it was completed by Queen Eleanor. She no doubt decided that if she must occasionally reside in this corner of Gwent, she should be able to worship in the type of church to which she was accustomed.

An architect from her own country was invited to design and build the church to suit her requirements. Traces of the Frenchman’s influence can certainly be seen. It was built in the form of a cathedral, cruciform in plan, with a fine octagonal tower (in which there are six bells) and a spire at the intersection of the transepts.

Grosmont was an important place at that time and deserved a house of worship in keeping with the splendours of the age. The castle was still in its prime and the church was built large enough to accommodate the garrison.

The large vestry on the south side of the chancel is still known as Queen Eleanor’s Chapel and it once contained the piscina, which is now built into the north wall of the north transept.

It is interesting that Queen Eleanor ‘the Rose of Provence’ was the first to adopt the red rose as the badge of her house. When in 1267, Edmund Crouchback, Earl of Lancaster was given the three castles (Grosmont, Skenfrith and White castle) by his father, King Henry, it acquired the name ‘Castle of the Red Rose’.

When Henry III died on November 16th 1272, having reigned for 56 years, the Knights Templar with the consent of the Queen undertook the care and expense of his funeral and burial in Westminster Abbey. Queen Eleanor then acted as regent until her son Edward returned from France.

In 1280, she retired to the Benedictine convent of Amesbury, Wiltshire, where she took the veil and assumed the religious habit of a nun on July 7th 1284. She died in 1291 after a short illness at the age of 67 with her son King Edward I at her bedside and was buried at the convent church. But her heart was buried in the church of Friars Minors (Minories), London.

Leave the church and turn left. Continue around the church to reach the rear. Half way along this side of the church, where the wall juts out, look out for a semi circular stone in the ground, which is supposedly the head stone of Jack of Kent’s grave.

Jack, according to local folklore, was a giant. There are many fascinating stories concerning his amazing deeds and regular contests with the devil. His final pact with Satan was that the he should take Jack’s soul when he died, whether he was buried in church or outside. However he fooled Satan by arranging for his burial to take place under the wall of Grosmont Church, so that in truth he was neither inside nor outside.

Continue to reach a tarmac path. Turn left and head up hill to the main gates and onto the village road. Return to your starting point.