Monmouth's main drag, such that it is, starts at car-free Monnow Bridge, the UK's only complete example of a medieval fortified bridge. It was built in 1270, although much of what you see now was restored in 1705. Before you cross into town, it's worth poking your head into St Thomas the Martyr's Church . Parts of it date from around 1180 – there's an impressive Norman Romanesque arch, and pews and a gallery fashioned out of dark wood.
When Catholicism was banned in Britain, Monmouthshire was a pocket of resistance. In the 16th-centur, secret Masses were held at the Robin Hood Inn , which still stands at the foot of Morrow St; apart from its historic connections, it's a great place for a pint or pub meal, with a big beer garden. In 1679 a Catholic priest, Fr (later St) David Lewis, was discovered, tried in Monmouth and hung, drawn and quartered in nearby Usk. In 1793, after the Catholic suppression ended, the first new Catholic church in Wales was built in Monmouth. Even then, St Mary's Church needed to be discreet and was hidden behind a line of cottages; they're now removed, explaining why it's set back from the road.
At the top end of Monnow St is Agincourt Sq, dominated by the arcade of the 1724 Shire Hall and a statue of former Monmouth resident Charles Stewart Rolls (1877–1910). One half of the team that founded Rolls-Royce, Rolls was not only a pioneering motorist and aviator, he was the first British citizen to die in an air accident (his statue is clutching a model of the Wright biplane in which he died).