How to spend 48 hours in Chepstow

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Chepstow combines the best of old and new. The city was a great medieval power with its Norman castle built at a strategic point overlooking the River Wye.

Do you like shopping? There are many independent shops in Chepstow, surrounded by historic Georgian and Victorian buildings.

Just down from the center 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 summer days.

Read more:Comfortable accommodation 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, shopping, nearby attractions, and independent dining.

We’ve rounded up some of the best things to do, places to eat, and accommodation options for a perfect weekend getaway in Chepstow.




What to do in Chepstow

You can’t visit the town without going to see the impressive Chepstow Castle – it is the oldest post-Roman castle in Wales dating back to 1067.

The city center is also full of unusual souvenir shops and a few antique shops, where you are sure to find great finds. Many cafes and restaurants are also to be discovered.

Nearby you will find the famous Chepstow Racecourse and the National Activity and Diving Center [NDAC], where you can try your hand at scuba diving.




Chepstow is a perfect town for hiking and gentle walks, with many long-distance trails starting here including the Wye Valley Walk, Offa’s Dyke National Trail, and the Wales Coast Path.

Hiking enthusiasts will love the Wye Valley Walk between Chepstow and Tintern Abbey. Climb ancient stone steps and hike ethereal forest trails. There are plenty of lookout points along the way where you can picnic and photograph the meandering River Wye.

Here are some of the highlights and the best things to do in Chepstow.

Visit Chepstow Castle



Chepstow Castle

Chepstow Castle is a beautifully preserved Welsh castle that stands proudly on a limestone cliff above the River Wye, having stood the test of time. It is a must-see place during a weekend in Chepstow.

Construction 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 Great Norman Tower, but construction work continued until the 17th century, with the medieval ramparts being replaced by more solid parapets suitable for muskets.

Today, visitors can learn more about this historic Cadw-run site by visiting this impressive castle on a day trip or by booking one of their special events. There are a range of facilities here, including a gift shop, bike access, and parking.

Paddle boarding on the River Wye



The River Wye is a long and very accessible river that runs through many villages and towns, including Chepstow. Along the river you will find plenty of paddleboarding spots and waterfront pubs and it’s also the perfect place to try your hand at paddle boarding.

Stand-up paddleboarding – or SUP – is a fun activity for the whole family and suitable for most ages and abilities.

You will definitely need to put in a lot of effort to stay upright and balanced when you start out. It’s pretty much guaranteed you’ll all fall into it at some point, so maybe grab a waterproof camera to capture the most hilarious failures.

Paddling gently down the river is a unique way to experience the beautiful Wye Valley scenery, spot wildlife, and get a great strength training all at the same time.

Several businesses in the region offer a range of SUP experiences for all ages, including the family business Inspire2Adventure.

Read more:11 epic paddleboarding sites in Wales to make the most of everyone’s new hobby

Take the Wye Valley Walk



There are many hiking routes and shorter hiking trails that can help you experience the beauty of the Wye Valley on foot. If you’re looking for a longer walk in Wales, opt for the Wye Valley Walk, a long-distance national footpath that follows the course of the River Wye.

You can choose different sections of the trail for day hikes and weekend hikes – or go for a full walking vacation and do it all. One of the best day hikes on the Wye Valley Walk is the Chepstow section at Tintern Abbey.

It’s a scenic eight-kilometer walk that takes you over ancient stone steps and through ethereal forest trails. There are plenty of places to take photos and have a picnic along the way and you’ll also find lookout points where you can look out over the meandering River Wye.

Autumn is the best time to try this trail – when the leaves start to change color it becomes one of the UK’s finest hiking trails. Pack a picnic to complete the country experience.

Go scuba diving at the National Diving and Activity Center




NDAC is a large flooded quarry in Tidenham near Chepstow where you can enjoy excellent scuba diving in clear waters. The quarry is approximately 700 meters long and at its deepest point is 80 meters. It is aimed at beginners and more experienced technical divers.

For older children who wish to try diving, NDAC offers introductory courses for adults and children; ranging from Try-Dives to the PADI / SDI Open Water Diver course.

This great site also has a bike rental, a water park, a zippered slide (for over 12s) that reaches speeds of up to 40mph and there is a giant 3D swing.

Explore Tintern Abbey




One of our largest monastic ruins, it is arguably the best-preserved medieval abbey in Wales. Tintern Abbey is 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 monasteries which led to the slow transformation of the abbey into a majestic ruin.

Today you can visit this important Wales heritage site and marvel at the scale of the roofless abbey and British Gothic architecture. Tickets can be purchased on arrival at the visitor center and there is also a selection of guides to purchase that can help you learn more about this beautiful abbey.

Walk the forest trails of Puzzlewood




Just a 20 minute drive from Chepstow you will find the ‘Puzzlewood’ ethereal forest.

It is such a unique and enchanting place that scenes from favorite movies like Star Wars and Merlin have been filmed here.

And JRR Tolkien is reputed to have taken his inspiration from the legendary forests of Middle Earth from Puzzlewood.

Located just across the Welsh border near Chepstow, you can explore a mile of winding footpaths and marvel at the fantastic tree and rock formations in the 14-acre ancient forest.




In addition to the woods, there are lots of animals, a willow maze, indoor mazes and a toddler running track, an outdoor play area, plenty of picnic benches, a cafe and a shop. of gifts with lots of local crafts. It is open every day all summer from 10 a.m. and the last entry is at 5 p.m.

Where to stay

There are a range of Airbnb properties, guesthouses, and hotels in Chepstow to suit your travel style and budget.

The George hotel in town costs £ 55 per night, or you can stay at Saint-Pierre-Marriot for £ 60 per night.

For something a little more private, there is this chalet available for £ 53 per night.

The Beauford Hotel is also available and is a historic, family-run inn in the heart of Chepstow which costs £ 85 per night. Here you will find excellent food (AA rosette) and a popular bar.

At National Diving and Activity Center (NDAC) you will find unique glamping pods located in a former quarry that has been converted into an awesome activity and diving attraction.

The site has a range of wooden wigwams that range from more basic pods to VIP Wigmam pods that include an exclusive hot tub on your own private terrace, luxury bathrobes and slippers, showers and toilets, TVs, towels and kitchen equipment. They have everything you need for a relaxing fall vacation.

For adventure seekers, why not try their scuba diving, zipline or giant swing activities, then retreat to your comfortable cabin for a quiet evening.




Further on is the charming Tudor Farm, which is about a 20 minute drive from Chepstow. This boutique hotel is a former working farmhouse that has been elegantly transformed into a country getaway with rooms, cottages and suites. The prices depend on the type of room booked.

You should not miss the opportunity to dine at Tudor Farmhouse. Their chef ensures that quality, locally sourced ingredients are used in their seasonal dishes.

Farmhouse meets upscale cuisine here with flickering candles, exposed stone walls, and lightly muted tones. It contrasts beautifully with the smell of homemade food that wafts through the dining room.



Where to eat

There are a few great places to eat in Chepstow, including Mango House, The pepper mill and Italian restaurant Panevino.

Or for something more relaxed there is the Stone Pizza restaurant.

As Chepstow is the gateway to the Wye Valley, you’ll find plenty of great restaurants, cafes and local producers in this popular foodie spot. The region has a growing reputation and a thriving food and beverage scene to explore.

You can travel seamlessly from Wales to England and easily explore the affluent region and its many restaurants, cafes and producers.



Local breweries include the small microbrewery Lydbrook Valley Brewing Company, producing a 4.2% IPA, and the Wye Valley Brewery, producing a decent range of craft beers.

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 resting place if you are heading up the river on an epic canoe or kayak tour while visiting Chepstow. The Boat Inn and Anchor Inn both offer local beers and a view of the river.



One of the best places for a pint by the water is the Saracens Head Inn. This historic riverside inn has occupied its spectacular position on the east bank of the River Wye for centuries, where the river flows into a rugged wooded gorge.

Here you will find rooms, award-winning cuisine and local beers.

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