What? A gentle walk to pair the medieval with the modern, complete with visit to a quaint market town and its medieval fortress

Where? Chepstow, Monmouthshire

Cadw site to see: Chepstow Castle and Tintern Abbey

Most ‘Instagrammable’ spot: Chepstow Castle’s upper bailey. Choose your favourite window and practice your best ‘candid’ pose as you look out across the River Wye.

Perched high above the banks of the River Wye, Chepstow Castle is the oldest surviving post-Roman stone fortification in Britain and is home to a pair of 800-year-old castle doors — the oldest surviving in Europe!

Begin your visit by exploring the castle, climbing the battlements and taking in the panoramic views across Monmouthshire before embarking on an afternoon walk. Follow signs from the Castle to the Wye Valley Walk, taking the paths past the town until you reach the woodland trails through Alcove Wood and Pierce Wood. If the mood takes you, this trail can lead all the way to Tintern Abbey, but for something a little more slow-paced, a visit to the local town may be more palatable.

Chepstow (which means ‘marketplace’ in Old English), is bursting with independent boutiques and unique home interior shops amid the handsome Georgian and Victorian buildings in the town centre. And, that’s not forgetting the abundance of quaint pubs, cafes and restaurants conveniently located on every street corner. Firm favourites include The Riverside Restaurant , which offers spectacular views across the River Wye. 

If you don’t have time to stop for food, the local high-street can be found bursting with colour on the second and forth Saturday of every month as Chepstow Farmer’s Market takes over the area — a great excuse to stock up on fresh, local produce for testing out a new recipe on your return home.