Chepstow blends the very best of ancient and modern. The town was a major medieval powerhouse with its Norman castle built at a strategic point overlooking the River Wye.
Love shopping? You'll find plenty of independent shops in Chepstow that are surrounded by historic Georgian and Victorian buildings.
Just down from the centre, you can cross the bridge between England and Wales, and the river is surrounded by a number of good pubs which make it a great spot on a summers day.
Read more:Cosy places to stay with hot tubs in Wales perfect for a winter break
It's an underrated town in the lower Wye Valley that deserves a full weekend to make the most of the scenic hikes, shops, nearby attractions and independent restaurants
We've rounded up some of the best things to do, places to eat and accommodation options for a perfect weekend away in Chepstow.
What to do in Chepstow
You can't visit the town without going to see the impressive Chepstow Castle - it's Wales' oldest surviving post-Roman castle that dates back to 1067.
The town centre is also full of quirky gift shops and a few antique shops, where you're sure to make some great finds. There are also plenty of cafes and restaurants to discover.
Nearby you'll find the popular Chepstow Racecourse and the National Activity and Diving Centre [NDAC], where you can try scuba diving.
Chepstow is a town that's perfect for hiking and gentle walks, with many long-distance trails starting here, including the Wye Valley Walk, the Offa's Dyke National Trail and the Wales Coast Path.
Hiking fans will love the Wye Valley walk between Chepstow and Tintern Abbey. Walk up ancient stone steps and through ethereal forest paths. There are plenty of viewpoints along the way where you can have a picnic and photograph the winding River Wye.
Here are some of the highlights and best things to do in Chepstow.
Visit Chepstow Castle
Chepstow Castle is a beautifully-preserved Welsh castle that proudly sits on a limestone cliff above the River Wye, having stood the test of time. It's a must-visit place when spending a weekend in Chepstow.
Building was started in 1067 by Earl William Fitz Osbern, a close friend of William the Conqueror, making it one of the first Norman strongholds in Wales.
The oldest building is the Norman great tower but building work continued well into the 17th century as medieval battlements were replaced by stronger musket-friendly parapets.
Today visitors can learn more about this historic site that's managed by Cadw by visiting this impressive castle on a day trip, or by booking onto one of their special events. There's a range of facilities here including a gift shop, bike access and parking.
Paddleboard on the River Wye
The River Wye is a long and very accessible river that flows through many villages and towns, including Chepstow. Along the river, you'll find plenty of paddle spots and waterside pubs and it's also the perfect place to try your hand at paddleboarding.
Stand-up paddleboarding – or SUP – is an entertaining activity for all the family and is suitable for most ages and abilities.
You will definitely need to put a fair amount of effort into staying upright and balanced when you start. It's pretty much guaranteed you'll all fall in at some point, so perhaps take a waterproof camera to capture the most hilarious fails.
Gently paddling down the river is a unique way of experiencing the beautiful scenery of the Wye Valley, spotting wildlife and getting a great core muscle workout at the same time.
There are several companies in the area that offer a range of SUP experiences for all ages, including the family-run company Inspire2Adventure.
Read more:11 epic paddleboard locations in Wales to get the best out of everyone's new hobby
Do the Wye Valley Walk
There are plenty of hiking routes and shorter walking trails that can help you discover the beauty of the Wye Valley by foot. If you are looking for a longer walk in Wales, plump for the Wye Valley Walk, a long-distance national trail that follows the course of the River Wye.
You can choose various sections of the trail for day hikes and weekend hikes – or opt for a full walking holiday and do the lot. One of the best day hikes on the Wye Valley Walk is the Chepstow to Tintern Abbey section.
It's a scenic, five-mile walk that takes you up ancient stone steps and through ethereal forest paths. There are plenty of photo and picnic spots along the way and you'll also find some viewing points where you can gaze at the winding River Wye.
Autumn is the best time to attempt this trail: when the leaves begin to change their colours it becomes one of the prettiest hiking trails in the UK. Pack a picnic to round out the country experience.
Go scuba diving at the National Diving and Activity Centre
NDAC is a large flooded quarry at Tidenham, near Chepstow, where you can enjoy excellent scuba diving in clear waters. The quarry is around 700 metres long and at its deepest point is 80 metres. It caters for beginners and more seasoned, technical divers.
For older children who would like to try diving NDAC have beginner's courses for adults and children alike; ranging from Try-Dives to the PADI/SDI Open Water Diver course.
This large site also has bike hire, aqua park, a zip slide (for the over 12s) which reaches speeds of up to 40mph and there's a giant 3D swing
Explore Tintern Abbey
One of our greatest monastic ruins, this is surely the best-preserved medieval abbey in Wales. Tintern Abbey is just a short drive from Chepstow, or you can walk from Chepstow to Tintern Abbey on the Wye Valley Walk.
It was founded in 1131 by Cistercian monks and has had a long history, including the dissolution of the monasteries which led to the abbey slowly turning into a majestic ruin.
Today you can visit this important heritage site in Wales and marvel at the scale of the roofless abbey and the British Gothic architecture. Tickets can be bought on arrival at the visitor centre and there is also a selection of guidebooks to buy that can help you learn more about this beautiful abbey.
Wander the forest trails in Puzzlewood
Just 20 minutes drive from Chepstow, you'll find the ethereal forest of 'Puzzlewood'.
This is such a unique and enchanting place that scenes from TV and film favourites like Star Wars and Merlin have been shot here.
And JRR Tolkien is reputed to have taken his inspiration for the fabled forests of Middle Earth from Puzzlewood.
Situated just over the Welsh border, near Chepstow, you can explore a mile of meandering pathways and wonder at the fantastic tree and rock formations in the 14-acre ancient woodland.
As well as the woods, there are lots of animals, a willow maze, indoor mazes and a toddler racing track, an outdoor playground, plenty of picnic benches, a cafe and a gift shop with lots of local crafts. It's open daily throughout the summer from 10am and the last entry is 5pm.
Where to stay
There is a range of Airbnb properties, guest houses and hotels in Chepstow to suit your travel style and budget.
The George Hotel in the town costs £55 per night, or you can stay at the St Pierre Marriot for £60 per night.
For something a little more private there's this cottage available for £53 per night.
The Beauford hotel is also available and is a family run and historic inn in the heart of Chepstow that costs £85 per night. Here, you'll find excellent food (AA rosette) and a popular bar.
At the National Diving and Activity Centre (NDAC) you'll find unique glamping pods situated in an old quarry that has been repurposed into an awesome activity and diving attraction.
The site offers a range of wooden wigwams which range from more basic pods through to VIP Wigmam pods that include, exclusive hot tub on your own private decked area, deluxe robes & slippers, shower and toilet facilities, TV, towels and kitchen facilities. They have everything you need for a relaxing autumn break.
For adventure lovers, why not try their scuba diving activities, Zipline or giant swing and then retire to your cosy cabin for a quiet evening.
Further afield is the charming Tudor Farmhouse, which is around a 20 minutes drive from Chepstow. This boutique hotel is a former working farm that has been stylishly converted into a country getaway with rooms, cottages and suites. Prices depend on the type of room booked.
You should not miss the chance to dine at Tudor Farmhouse. Their head chef ensures that quality and locally-sourced ingredients are used in their seasonal dishes.
Farmhouse meets upscale dining here with flickering candles, exposed stone walls, and slightly hushed tones. This contrasts beautifully with the scent of homemade food wafting the dining room.
Where to eat
There are some great places to eat in Chepstow, including Mango House, The Pepper Mill and Panevino Italian Restaurant.
Or for something more relaxed, there's the Stone Rock Pizza restaurant.
As Chepstow is the gateway to the Wye Valley, you'll find plenty of quality restaurants, cafes and local producers across this well-known foodie hotspot. The area has a growing reputation and a thriving dining and foodie scene to be discovered.
You can criss-cross seamlessly from Wales into England and explore the well-heeled area and its many restaurants, cafes and producers with ease.
Local breweries include small microbrewery Lydbrook Valley Brewing Company, producing a 4.2% IPA and the Wye Valley Brewery, producing a decent range of craft ales.
The Wye Valley even has its own vineyard in the form of White Castle Vineyard, where visitors can buy Welsh wines and also tour the small vineyard.
There are numerous pubs along the River Wye which are a welcome rest spot if you're paddling up the river on an epic canoe or kayak trip whilst visiting Chepstow. The Boat Inn and the Anchor Inn both offer local ales and river views.
One of the best spots for a pint by the water is the Saracens Head Inn. This historic, riverside inn has stood for centuries in its spectacular position on the east bank of the River Wye where the river flows into a steep wooded gorge.
Here you'll find rooms, award-winning food and local ales.
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