The castle stretches along a narrow limestone ridge above the River Wye, and it has been there since 1067, which makes it the oldest surviving post-Roman stone fortification in Britain. Most Norman lords started with timber and upgraded later. William FitzOsbern built this one in stone from the first.
Below it, on the river, is the Boat Inn, said to be over 500 years old and to have been several different things across those years. It pours up to four ales and keeps a large gin selection, and there's live music every Thursday. One TripAdvisor reviewer called it "a hidden traditional pub," which is the sort of thing people say about a pub on a riverbank they'd rather keep to themselves. The garden runs down to the Wye, a river with one of the highest tidal ranges in the world, so the view is never quite the same twice.
Up the hill the pubs multiply. The Chepstow Castle Inn sits at 12 Bridge Street doing traditional pub food near the walls. The Five Alls has served the town for over 176 years and gives CAMRA members ten percent off, with a large beer garden out the back that has a view worth the walk. The Two Rivers leans gastropub, with premium ales and a rotating list of guests.
For food to take home there's the Sunday market in Beaufort Square and along the High Street, artisan stalls on the second and fourth Sundays. Just over the river at Tidenham, Hanley Farm Shop runs a deli, cafe and butchery, and Newhall Farm Shop at the garden centre keeps its own butcher and a fish counter.
The walking is the reason to stay. The Wye Valley Walk finishes here after 136 miles from mid-Wales; the Chepstow–Tintern stretch is about six wooded miles. Offa's Dyke Path runs up the far bank, so you can loop out through England and back through Wales. From the castle, the Lancaut peninsula walk takes you round a river loop "lost in time," along clifftops where peregrines nest, down to a ruined church. The 18th-century tourists who walked the Piercefield viewpoints — the Alcove, Giant's Cave, Lover's Leap, Eagle's Nest — were doing what Visit Monmouthshire calls "the birthplace of British tourism."
The Priory Church of St Mary is worth a look for the Norman west doorway, all zigzag and chevron. The original central tower blew down in a storm in 1701 and took the transepts with it; the replacement, finished in 1706 under a vicar named Thomas Chest, has been described as "an amusingly rustic classical idiom."
The town is easy to reach. Chepstow station is on the Gloucester–Newport line, roughly hourly, with the bus station about 550 yards off. The M48 runs west to Newport, and the A466 north up the valley to Tintern and Monmouth. The Old Wye Bridge, cast iron from 1816, still carries traffic across to England.
Each midwinter the town carries the Mari Lwyd house to house — a decorated horse's skull, singing at doors for entry. It has been doing this a very long time, and shows no sign of stopping.