Top 10 things to do in Monmouthshire

Here are our top ten things to do in Monmouthshire. We're deliberately focusing on simple down to earth experiences because that's what we’ve come to value over the past few years. 

#1 Visit Chepstow Castle

There’s no better place in Britain to see how castles gradually evolved to cope with ever more destructive weaponry – and the grandiose ambitions of their owners. Chepstow castle was the first stone built castle in Wales and is now the oldest stone fortification in Britain.

#2 Walk up the Sugarloaf

Visible between the ridges of the Llanwenarth, Deri and Rholben hills, the Sugarloaf is one of the highest peaks in the Black Mountains. It stands at 596m and offers wonderful panoramic views across the Brecon Beacons, South Wales, and towards south-west England.

Although its iconic shape is volcano-like, the Sugarloaf is made of the same old red sandstone as the rest of the Black Mountains.

#3 The Kymin

A charming 18th-century Round House and Naval Temple stand proudly on top of the Kymin and its nine acres of pleasure grounds, overlooking Monmouth and the beautiful Wye Valley. Pack a picnic of local produce and enjoy it in the grounds of the Round House, built in 1794 by Monmouth Picnic Club to provide a breathtaking spot for lunch.

#4 Visit an award-winning vineyard

Enjoy tours and tastings at one more of our four award-winning vineyards:

• Ancre Hill Estates - making high quality wine utilising traditional Biodynamic and Organic Viticultural practices
• Parva Farm Vineyard –a small friendly vineyard producing award-winning wines, meads and sparkling wines, overlooking Tintern Abbey in the beautiful Wye Valley
• Sugarloaf Vineyards – producing award-winning wines on the slopes of the Sugarloaf mountain, licensed coffee shop on site.
• White Castle - Gold award winners at Decanter world wine awards 2021, this 7 acre vineyard is planted on the gentle slopes of the beautiful rolling countryside of Monmouthshire, near Abergavenny.

#5 Visit Tintern

No visit to Monmouthshire would be complete without visiting Tintern in the heart of the Wye Valley Area of Outstanding Natural Beauty.

After your visit to the Abbey (which is a must see) there are some lovely independent shops, pubs and eateries, as well as a vineyard and a Victorian railway station to visit. The village is also a hub for walkers and cyclists with a number of circular routes and long distance trails starting / passing though.

The whole village is dog-friendly so your four-legged friend will receive a warm welcome too.

#6 Climb the Skirrid

An energetic walk, best done on a cold, crisp winter’s day. This walk takes you through woodland into open mountainside, before a steep climb to the summit with panoramic views of the surrounding countryside.

#7 Visit Raglan Castle

Play Kings and Queens at this magnificent castle, designed more to impress than intimidate.

#8 Experience the excitement of a day at the races

A day at Chepstow Racecourse is as casual or as formal as you want to make it. For some it’s a get together with friends, for others it’s an excuse to dress up, especially on Ladies Night when many ladies get dressed up and wear hats – not obligatory, but great fun! Families are always welcome with accompanied children under 18 entering for free and free entertainment on certain days.

#9 Visit White Castle

White Castle is the best preserved and most imposing of the trio of Monmouthshire fortresses known as the ‘Three Castles’ – which includes Grosmont and Skenfrith – built to control the border. If you’re feeling energetic follow the Three Castles 19 mile circular route linking the three medieval castles.  

#10 Monnow Gate & Bridge

Visit the only remaining medieval fortified river-bridge in Great Britain with its gate tower still standing. Once used as a gaol. Tours available from Shire Hall.