Chepstow is a small town, with a population of just under 15,000, located in southern Wales in the United Kingdom. It’s by no means a big city with unceasing nightlife, but there are plenty of interesting things to do and see for it to be a perfectly nice destination for a family holiday. (Unless you have twenty-something children who need unceasing nightlife that is!)

Credit: Image courtesy of Roy Parkhouse


Archeological investigations in the area have revealed that humans have inhabited the area that we now know as Chepstow since as long ago as 5000BC! The town is situated around Chepstow Castle, one of the most ancient castles in the UK, which was built in the 1200s.

History Of Chepstow
Credit: Image Courtesy of National Library of Wales. Original Author: George Rowe, 1850.

Throughout history, from the Middle Ages right up to the present day, Chepstow has been a bustling, successful town - making an existence from first wine imports and timber and bark exports; then tourism; then shipbuilding and other forms of heavy engineering.


Nowadays, it is the peaceful, relaxed home of many workers from bigger cities - Newport, Cardiff and Bath - who commute to work along the nearby main road, the M48.



  • More than 100 shops in or around the town centre - a great piece of parental ammunition for keeping teenagers entertained/ bribing them to come on holiday with you at all.
  • Plenty of parking means you won’t have to endure the long trudge from some out of town layby.
Chepstow Highstreet
Credit: Ghmyrtle
  • Numerous bars, restaurants, cafes and hotels - at least one of them must have something that (s)he’ll eat!
  • A choice several national supermarket - just in case the restaurants don’t do the trick and you have to stock up on extra munchies. Choccy biccies anyone?
  • And even a weekly farmers’ market to stock up on fancy produce for the work staffroom when you get back!

Things to do

  • Twice yearly community festival.
  • Yearly agricultural show.
  • Watch the horse racing at Chepstow Racecourse which has been hosting the Welsh National since 1949.
Chepstow Racecourse
Credit: Stuart Wilding
  • Go swimming or take part in in/outdoor sporting activities at the leisure centre.
  • Visit the castle which is open most days apart from bank holidays each year. Within there’s loads of fascinating information on the origins of the castle. Once you’re done you can take in a short stroll along the adjoining footpath, which makes up part of the Wye Valley Walk.
  • Visit the town gate. The Gate House is open for the public to visit. If you go to the castle as well, then you could potentially have a whole day of fun-filled taking in the history of the area. Really, mum?
Chepstow Castle
Credit: Dennis Turner
  • But that’s all boring compared to my personal favourite: “Hoggin’ the Bridge”. This charity event takes place every October and consists of what seems like millions of motorbikes and riders riding across the Severn Bridge and into Chepstow town centre. Definitely an idea for a day out that’ll keep even your un-entertainable male teenager entertained. Remember to bring the gas masks though!
  • Or if it’s too rainy for any of that - an all too regular occurrence in Wales! - then you could just listen to some Chepstow Radio. That’s right, they even have their own radio station!
  • And once the sun comes back out you could just go for a walk; follow your noses and take in all the beautiful scenery, buildings and sometimes even weather(!) that Chepstow has to offer.