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Chepstow is a picturesque Welsh market town situated at the southernmost point of the Anglo Welsh border. It marks the southern starting point of the much cycled and trekked Offa’s Dyke path which has historically acted as the dividing line between Wales and England. It also sits just on the edge of two of the UK’s most renowned areas of natural beauty, the Wye Valley and Forest of Dean. This area of the country has inspired writers and poets for centuries such as William Wordsworth, Dennis Potter, J.R.R Tolkien, and most recently J.K Rowling author of the Harry Potter books who lived and went to school nearby. Many tv series and films have also been shot on location in the Forest of Dean, including Robin of Sherwood, Dr Who, Atlantis, Merlin and Jack the Giant Slayer. Most famously of all, Star Wars The Force Awakens was shot at local beauty spot and tourist attraction Puzzle Wood. This part of the World stimulates minds and nurtures creativity, and once you spend any time here, you’ll begin to understand why.

Chepstow and its surrounding area is an increasingly popular tourist destination due to its well preserved Norman Castle which is arguably the oldest surviving stone fortification in Britain. The Chepstow racecourse hosts the Welsh Grand National, regular race weekends and outdoor concerts throughout the year whilst historic Tintern Abbey is just a short drive away on the Wye Valley route to Monmouth.

Chepstow is also a convenient distance from the cities of Bristol and Cardiff making it an ideal place for those wanting to experience those cities without having to stay in the centre of either of them.

Chepstow also has a vibrant music scene with many bars hosting live gigs, and its summer festival providing regular concerts within the grounds of the castle. Many internationally renowned acts including Tom Jones, UB40, Madness and Simply Red have performed in recent years at Chepstow racecourse helping it to become one of the best outdoor concert venues in Wales.

The National Diving and Activity Centre also sits on the edge of the town, which is one of the country’s deepest and biggest inland diving centres. It also offers other outdoor activities like a giant zip-line, flyboarding, a 3G swing and, during the summer an outdoor drive-in cinema. So all in all we think Chepstow is the perfect stop off whilst exploring South Wales and the West of England, but then again, we at The First Hurdle are a little biased!

Chepstow Castle

Chepstow Castle

For more information about the history of Chepstow Castle click here and visit the CADW website.

Chepstow Racecourse (Welsh National)

chepstow racecourse

For information on future events check Chepstow Racecourse’s Website

Tintern Abbey

tintern abbey

For more information please click here.

Wye Valley

Wye Valley

For more information please click here.

Forest of Dean

Puzzle Wood

For more information about the Forest of Dean please click here to visit their website.

For more information about Puzzle Wood please click here to visit their website.


The First Hurdle Bristol

For information please click here to visit the official tourist guide website.

Visit Bristol


Cardiff Principality Stadium

For information on the city of Cardiff please click here to visit the official tourist guide website.

For information on Principality stadium tickets, matches and events click to visit their website.

Millennium Stadium Cardiff