Southeast trail/Llwybr De-ddwyrain
Abergavenny Castle/Castell Abergavenny
A Norman castle was on this site in 1081. The remains today include a fourteenth century gatehouse and four towers. Abergavenny museum in the castle grounds. The castle in the late twelfth century is noted for the treacherous deed undertaken by William de Broaose in 1175 when he invited Seiyllt ap Dyfnwal and other prominent Welsh guests to celebrate Christmas. He had the Welsh guests murdered and then attacked Seisyllt ap Dyfnwal's Castell Arnallt where he had his wife and child killed. This inspired a Welsh rebellion with Abergavenny castle being burnt. The castle is in the town of Abergavenny on the A40.
White Castle (Llantilio Castle)/Castell Gwyn
This is a twelfth century castle on an earlier Norman site. The remains seen today are mainly from the thirteenth century with outer bailey defences and include large twin towered gatehouse and four D-shaped towers surrounded by a moat. The site is about eight miles northeast of Abergavenny off the B4521.
Raglan Castle/Castell Rhaglan
This is a fifteenth century castle and building began on the site of a previous manorial site in 1435. A significant feature of the castle is the 'Great Tower' which was heavily damaged in the English Civil War. It is surrounded by a wall with corner turrets and an impressive double towered gatehouse. The castle is located at Raglan off the A450 southeast of Abergavenny.
Monmouth Castle/Castell Trefynwy
Originally built in the mid eleventh century the remains seen today are mainly the twelfth century tower, thirteenth century great hall and parts of the castle walls. It is located in Monmouth off the A40.
Harold's Stone Rowe
These three large standing stones are off the A466 south of Monmouth near the village of Trelleck along the B4293. These stone are aligned and stand at different angles.
Chepstow Castle/Castell Cas-gwent
This site overlooks the River Wye and the first Norman castle was built in stone here in the late eleventh century. It was further fortified and rebuilt in the late twelfth century with the addition of walls and towers and residential apartments and these are many of the remains seen today. It was the site of military action during the English Civil War and is located in Chepstow off the A48.
Chepstow, Bulwark Camp
This is a late Iron Age site and made up of an enclosure with a double bank and ditch bordering the River Wye. It is located off the A48 at the end of Alpha Road in Chepstow.
Caerwent Castle/Castell Caerwent
Caerwent contains the remains of a substantial Roman settlement covering an area of some forty-four acres and there are significant remains from that period. The castle is now thought to be a fort site from that era. The site is southwest of Chepstow off the A48 towards Newport.
Caldicott Castle/Castell Cil-y-coed
Built on the site of a late eleventh Norman motte and bailey castle is an early thirteenth century stone keep, corner towers and curtain wall. A gatehouse was later added.in the fourteenth century. The castle had significant restoration undertaken in the nineteenth century and is an impressive site standing in large landscaped grounds. It is located at Caldicott off the A48 between Chepstow and Newport.
Llanmelin Wood
This large Iron Age hillfort has numerous banks and ditches and is located in a highly defensible position. The site is north of Caerwent off the A48 on a minor road where the site is reached by track and then footpath.
Grey Hill
This stone circle is made up of thirteen low stones standing adjacent to each other. There is a lone stone of about six feet outside of the circle and a further outlier. The site is off the A48 about four miles north of Caerwent.
Caerleon Castle/Castell Caerllion
A Norman late eleventh century motte and bailey castle stood on this site and the remains of this and the ruins a later thirteenth century tower can be seen. It is on private land in Caerleon north of Newport but can be viewed from the B4236 road close by.
Newport Castle/Castell Casnewydd
This castle dates from the fourteenth century and is located in Newport beside the River Usk. The remains seen today are the east front and towers.
Gaer Hillfort
This large circular hillfort enclosure site is surrounded by banks and ditch. It is in a commanding position over the River Ebbw. It is west of Newport toward Bassaleg at the end of Gaer Park Avenue.
Gaer Llwyd/Garnllwyd
A dolmen made up of the remains of a chambered tomb about twelve feet in length with a large broken capstone. It is located close to Llangwm on the B4235 Chepstow to Usk road.
Usk Castle/Castell Brynbuga
This was an early twelfth century earthwork site and a square stone keep, round tower and parts of a curtain wall survive. The castle is rectangular with curtain wall and towers with a three story gatehouse, great hall and overlooks the River Usk . It is located on the B4598 at Usk east of Pontypool.
Caerphilly Castle/Castell Caerffili
Caerphilly Castle is one of the largest and most impressive surviving fortresses from medieval Europe and is in thirty acre grounds in the centre of Caerphilly. Construction of this concentric Norman castle began in 1268 and had to stand against considerable Welsh attack. It is surrounded by water and a curtain wall with an inner ward with round corner towers and has a twin towered gateway. The outer ward has an impressive late thirteenth gatehouse. Considerable restoration was undertaken by the Bhute family in the nineteenth century. The site is in Caerphilly, which is north of Cardiff.