Chepstow is located in Monmouthshire, South Wales between the towns of Caldicot to the south west and Lydney to the north east. The town claims to be the "first historic town in wales" and it's position on the west bank of the River Wye, the river that forms the Anglo Welsh border, seems to prove the point.

Attractions include Chepstow Castle, the Town Gate, the Offa's Dyke Path, Wye Valley Walk, Chepstow Racecourse, Chepstow Bridge, and St Mary's Church. There is a good selection of shops in the town centre, plenty of places to stay and a number of quality restaurants in Chepstow. The banks of the Wye have been attractively landscaped and the town holds both a biennial festival and an annual folk festival.

Chepstow Castle, believed to be one of the oldest stone built fortified castles in Britain, is evidence of the strategic importance placed on Chepstow by William the Conqueror after his conquest of England in 1066. Within a year of the conquest William had sent his close friend William Fitz Osbern, Earl of Hereford, to build the massive hall known as the Great Tower on top of the limestone cliffs of Chepstow. By building the castle on the Welsh side of the Wye the Normans were demonstrating that they were the overlords of Wales as well as England. But the Normans did not have everything their own way with the Welsh proving harder nuts to crack than were the English. Chepstow Castle saw more than it's fair share of action during the next 400 years as many battles were fought over the green fields of Wales and the wild Marcher lands of the border country.

Chepstow Racecourse is probably most famous for hosting the Welsh National, a handicap chase that is often contested by horses which also run in the Grand National at Aintree. There are twenty-two fences to be jumped in the race. The ground conditions are often testing with stamina at a premium.

Other attractions include the southern point of Offa's Dyke Path, which begins on the east bank of the Wye at Sedbury Cliffs and runs all the way to the Irish Sea in north Wales. The Dyke was built in about the 8th century as a boundary between the English and Welsh kingdoms.
Another somewhat shorter walk is the Wye Valley Walk that runs along the Welsh bank of the Wye as far as Monmouth before leaving Wales and continuing into Herefordshire. The lower section of the walk includes the Eagle's Nest viewpoint which at 800 ft benefits from spectacular views of the Wye Gorge and the great bridges over the River Severn.

The Parish and Priory Church of St Mary was founded by the Normans in the 11th century (Fitz Osbern somehow finding time to build the church while building Chepstow Castle). However following the Dissolution of the Monasteries the church fell into neglect. The tower collapsed in 1700 followed by an unsympathetic restoration in the 19th Century. But St Mary's is still worth a visit as the nave remains in service as part of the parish church and the west tower built in the 18th Century incorporates a richly decorated Norman doorway.

The Town Gate originally built in the late 13th Century but much rebuilt, stands guard over the upper end of the medieval town. Fortunately the intricate street pattern of the old town has suffered little from "the developers" that have ruined so many of Britains historic towns.

The cast iron Chepstow Bridge was built in 1816 by John Rennie.

Chepstow Museum sits opposite the Castle entrance and occupies the rooms of a fine 18th Century mansion. The museum displays tell Chepstow's history from being one of Wales'largest ports, a shipbuilding centre, to a market town. Basketwork fish traps on display in the museum are evidence of Chepstow's links to the catching of the famous Wye salmon.