Monnow Bridge is a stone bridge with a gatehouse sitting in the middle of it, built around 1300 and now the only fortified river bridge left in Britain. You cross it on foot to get into the old town. It was designed to control who came and went, and these days it mostly controls where people stand to take photographs.
The town proper spreads up Monnow Street from the bridge, on a low spur of land where the Monnow runs into the Wye. This is two miles from the English border and, being low-lying between two floodplains, it floods. The Welsh name, Trefynwy, means "Town on the Monnow," which is about as much as a name can be asked to do.
Monnow Street is where the shops are. The Marches Delicatessen sells chutneys, jams and local spirits including Monmouth Gin and Silver Circle. A few doors along, Fingal-Rock is a wine merchant run by Tom Innes, a former barrister who opened it in 1987 as a cheese shop and switched to wine only in 2003; Burgundy is his subject. There's a third-generation butcher at number 34 selling meat from farms in Herefordshire and Monmouthshire, and a cluster of four shops at 31–33 run by Cath and Brenda Elsmore — a cook shop, a café, a toy shop, and a clothing and gift shop, which between them cover most eventualities.
For a pub, the Robin Hood Inn is the oldest thing here, or near enough — two low beamed rooms behind a wide Tudor arch, entered through a great wooden door. For over a century an upstairs room was used for secret Catholic masses, and in 1778 it was licensed as a "Publick Catholic Chapel." Traces of the religious paintings turned up under the plaster in the last century.
On Agincourt Square, the Punch House pours Wye Valley Butty Bach and was named Wales's Most Dog Friendly Pub by Rover.com. The Gate House sits by the bridge, overlooking the river.
St Mary's Priory Church has an octagonal needle spire with a gilded cockerel weather vane 205 feet up — the tallest thing in town. Pevsner's John Newman called it "large and austere." Inside is one of the largest collections of Nelson memorabilia anywhere, left by Lady Llangattock. Nelson himself came in 1802, dined on the square, and remarked, "To be known at such a little gut of the river as the Wye fills me with astonishment."
Two other men from here travelled further. Geoffrey of Monmouth wrote his History of the Kings of Britain around 1136 and more or less invented the King Arthur legend. Charles Rolls, of Rolls-Royce, has a statue on Agincourt Square; he died in a plane crash in 1910, aged 32. Henry V was born in the castle in 1386.
The walking is the reason many people come. The Peregrine Path runs level along an old railway line to Symonds Yat, buggy-friendly and flat. A steeper 7.5-mile circular climbs to the Kymin, where the National Trust keeps an 18th-century Round House and a Naval Temple, and returns along Offa's Dyke.
There is no railway station. All four lines closed by 1964, and the Troy station building was carted off and rebuilt in Gloucestershire, where it still stands, doing someone else's job.