A pleasant road leads from Chepstow station to Beaufort Square, in the centre of the town. After reaching it, those who have only a limited time to spend here may follow one of two courses : either turn to left along High Street and under the Gateway of the Town Wall, then to right along Welsh Street to the Castle Dell ; or turn to right and descend Bridge Street to the Castle entrance. The former is by far the more picturesque route, and by ascending the bank on the left side of the Castle Dell, and approaching the north-west corner of the mighty pile, where an elevated piece of ground overlooks the river, one obtains a striking view of the ancient walls rising sheer from riverside cliffs, with Piercefield Woods facing them.

The entrance to the Castle, however, is at the other (eastern) end, and is most easily reached by the other route. Sixpence is charged for admission.
As you face the magnificent entrance-gateway, the massive drum-tower at the angle to your left is that named Marten's Tower, after Henry Marten, one of the signatories to King Charles I's death warrant, who was a prisoner here for twenty years. After entering the first court by the strongly-plated door, one may inspect this tower, which has a little chapel in the upper storey. On the opposite side of this court are the banqueting hall and kitchen.

A covered way leads past Jeremy Taylor's Tower, where the author of Holy Living and Holy Dying was for a time kept in durance, into the second court, at the end of which stands the original Keep. Here one may see, preserved in the walls, many Roman bricks and tiles from an older fortress.

Beyond the Keep are two other courts separated by a deep fosse, and at the west end is a massive gateway, with the grooves for its triple portcullis still well-preserved. From the various embrasures one gains delightful peeps over the river towards the graceful road-bridge. The Dell already alluded to, on the south side of the castle, is a natural ravine of which the castle builders took advantage. In recent years it has been planted with many trees, and makes a very pleasant public resort.

Some kind of fortress stood in this situation from early British times. At the time of the Conquest a castle was built here by that famous warrior, William Fitzosbern. This original Norman fortress consisted of a central keep with narrow wards (the present second and third courts) on either side of it. In Edward I's time two other wards were added, one at each end (the first and fourth courts) : the keep was degraded into a hall, and the easternmost ward was made the castle's strongest portion. The peculiarity of the castle's construction is due to its position on a narrow tongue of rock between the Wye and the Dell.

After passing through various vicissitudes, the Castle was granted, in the days of Edward IV, to the Herberts. One of the Herbert ladies married Charles Somerset, Earl of Worcester, through whom the property descended to the Dukes of Beaufort. Some few years ago the property was sold to Mr. W. R. Lysaght, the present owner.

From the road bridge near the Castle one gains a good idea of the tremendous rise and fall in the river, high-water mark being plainly seen on the side of the cliffs. A tidal " bore " here ascends the Wye.

The Parish Church is reached from Beaufort Square by St. Mary's Street. The glory of the exterior is the Norman western doorway with the arcaded windows above it ; within, the fine proportions of the Norman nave are much admired. These are portions of the original church, which was that of a Benedictine priory. Immediately on the left, as one walks up the nave, will be noticed the tomb and effigies of the second Earl of Worcester and his wife. Under the tower is a slab to Henry Marten, the regicide, with an inscription composed by himself. Near the church will be noticed picturesque old almshouses.

Chepstow is fortunate in having retained its mediaeval Town Walls. These may be seen in very fair preservation on the western and southern sides of the town. There are drum-towers at intervals. The Town Gateway has already been mentioned. For the rest, Chepstow is an exceedingly quaint old town, with all sorts of curious courts and alleys, and at the same time well provided with comfortable hotels and refreshment-houses.

As regards sport, there are facilities for Hunting, Fishing, Golf, and outdoor games, including Tennis ; and, of course, there is a Picture-House for indoor amusement. The Chepstow country is hunted by Mr. Curre's Fox Hounds, celebrated as the whitest pack in Britain.