Must do in and around Chepstow

Chepstow’s Great Tower keep was commissioned by William the Conqueror barely a year after the Battle of Hastings, making this Britain’s oldest surviving post-Roman stone castle. Three major building phases followed. Overlooking the Wye, its position was highly strategic. We don’t mind a bit if you pop across to the English side of the river – the views from there are fantastic.

Chepstow, which means marketplace in Old English, offers relaxed, niche shopping in arty surroundings. Lined with handsome Georgian and Victorian buildings, the heart of town was made even more appealing in the mid-2000s. An award-winning scheme added pedestrian areas and intriguing stone walls and sculptures, inspired by local lore.

On Bridge Street, near the castle, this substantial Georgian townhouse has nostalgic displays on the history of Chepstow and the River Wye. There are photos and artefacts relating to fishing and shipbuilding, and paintings by artists who toured the Wye Valley’s most romantic spots in the 18th and 19th centuries.

Chepstow’s stone wall, built in the 13th century, used to have a main gate with a portcullis, where toll collectors would extract taxes from anyone bringing merchandise into town. The gate that stands today is a youngster at 500 years old. You can stroll through for free, no matter what you’re carrying.

This Regency road bridge has carried traffic from Chepstow to Gloucestershire since 1816. With massive pillars topped by five arches of gracefully curved cast iron, it crosses one of the world’s most tidal stretches of river. Between high and low tide, the Wye can drop by almost 15 metres.

St Mary’s is the earliest example of Romanesque architecture in Wales. Founded in the 11th century as part of a Benedictine priory, it’s similar in age to the Norman keep of Chepstow Castle. It’s been altered over the centuries, but the intricately decorated sandstone arch over the west door is unmistakably Norman.

From Chepstow Castle car park, a 17-mile waymarked walk meanders all the way to Monmouth via the Lower Wye. This wooded gorge is both a Site of Special Scientific Interest and an Area of Outstanding Natural Beauty. If the distance sounds a bit challenging, you could just sample a section.

Famous as the home of the Welsh National, which takes place each December, this top horse racing venue also hosts charity events and concerts. The hilarious Camel Derby held here in November 2013 raised over £40,000, and Tom Jones topped the musical bill in summer 2014.

The country estate of Piercefield House, once a grand neoclassical mansion, was a favourite haunt of 18th and 19th century artists such as Gilpin, Sandby, Lucas and Madeley. They set up their easels at its viewpoints to capture the Wye and the romantic ruins of Chepstow Castle in paint.

The sublime ruins of Tintern Abbey are less than six miles from the centre of Chepstow by bike, bus or car. From here, you can cross the Wye footbridge for a lovely woodland walk. Head for the Offa’s Dyke Path to Devil’s Pulpit, which offers dramatic views back to Tintern.