Chepstow, a border town in Wales, is home to the country's oldest surviving post-Roman stone castle, dating back to 1067, and offers a range of leafy walking trails ideal for autumn visits. Located on the border with England, the underrated castle town has serious medieval credentials, with its Norman castle built straight into a limestone cliff, standing guard over the winding River Wye.
Historic castle and town
Known as the “gateway to Wales,” the town gets its name from the Old English 'chepe stowe' or 'market place'. The name still fits as Chepstow keeps its historic feel with cobbled streets and a strong line-up of independent shops, cafés, restaurants, and pubs.
At the centre, Chepstow Castle is Wales' oldest surviving post-Roman stone castle dating back to 1067. For more than six centuries, Chepstow was home to some of the wealthiest and most powerful men of the medieval and Tudor ages. Earl William FitzOsbern, 1st Earl of Hereford and relative and close counsellor of William the Conqueror, began building it in 1067, making it one of the first Norman strongholds in Wales.
In turn, William Marshal (Earl of Pembroke), Roger Bigod (Earl of Norfolk), and Charles Somerset (Earl of Worcester) all made their mark before the castle declined after the Civil War. The oldest building is the Norman great tower, but construction continued well into the 17th century as stronger, musket-friendly parapets replaced medieval battlements.
Today, visitors can learn more about this historic site, which Cadw now manages, by visiting the castle on a day trip or booking one of its special events. There are a range of facilities here, including a gift shop, bike access, and parking.
Museum and walking trails
Continuing the history education, visitors can learn more about Chepstow's many industries at the museum housed in an elegant 18th-century house built by a prosperous merchant family. The museum's displays with atmospheric settings offer insight into Chepstow's wine trade, shipbuilding, and salmon fishing. Here, you'll find photographs, programmes, and posters recalling local people's pastimes, while 18th- and 19th-century paintings and prints illustrate the lasting appeal of Chepstow and the Wye Valley to artists and tourists.
Another big draw is the surprising range of leafy walking trails, with four long-distance walks converging on Chepstow. The Wye Valley Walk and Offa’s Dyke head north on either side of the River Wye, offering hikers a circular loop between Chepstow and Monmouth. Strolls around Tintern offer dreamy views of the romantic ruins of Tintern Abbey, especially from the Devil’s Pulpit viewpoint. A gentle riverside path from St Michael's Church to Tintern Old Station and the old railway line to Brockweir offers an easy, family-friendly amble.
If you download the AllTrails app, you'll find a range of routes in and around Chepstow that you can download and navigate from your phone. Chepstow is also a 'Walkers are Welcome' town, so visit the local Tourist Information Centre if you need help or guidance on where to walk. They also host the popular Chepstow Walking Festival every April.
Racecourse, golf, and outdoor activities
If you fancy a flutter, Chepstow’s got you covered. The town’s racecourse is a huge deal in the horseracing world and home to the Coral Welsh Grand National. It’s been hosting race days since the late 1800s and still draws a lively crowd whether you're a seasoned punter or just there for the buzz and fancy hats.
If horse racing doesn’t float your boat, you can swap the saddle for a nine-iron. Just outside town, the St Pierre Marriott Hotel & Country Club is one of the most scenic golf courses in the country. For years it hosted the British (formerly Dunlop) Masters, welcoming top players from around the world. Even if your swing’s a bit rusty, the views alone are worth the effort.
After plodding around the town, discovering indie shops and cobbled streets, why not head out into the wider Wye Valley area where you'll find hiking, kayaking, rock climbing, and paddleboarding? Plenty of ambitious hiking routes and shorter walking trails can help you discover the beauty of the Wye Valley on foot. If you want a longer walk in this area, opt 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 it all. 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. Plenty of photo and picnic spots line the way, and you'll also find viewing points where you can gaze at the winding River Wye. Autumn is the best time to attempt this trail: when the leaves change their colours it becomes one of the prettiest hiking trails in the UK. Pack a picnic to round out the country experience.
Tintern Abbey and Puzzlewood
One of our greatest monastic ruins, Tintern Abbey is surely the best-preserved medieval abbey in Wales. It is just a short drive from Chepstow or you can walk from Chepstow to Tintern Abbey on the Wye Valley Walk. Founded in 1131 by Cistercian monks, it has a long history including the dissolution of the monasteries, which slowly turned the abbey 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. You can buy tickets on arrival at the visitor centre, and a selection of guidebooks can help you learn more about this beautiful abbey.
For river activities, the River Wye is a long and accessible river that flows through many villages and towns including Chepstow. You'll find plenty of paddle spots and waterside pubs along the river, and it's also the perfect place to try paddleboarding. Stand-up paddleboarding (SUP) is an entertaining activity for the whole family and suitable for most ages and abilities. When you start, you need to put in a fair amount of effort to stay upright and balanced. It's definitely trickier than it looks. Gently paddling down the river is a unique way to experience the beautiful scenery of the Wye Valley, spot wildlife, and get a great core muscle workout. Several companies in the area, including the family-run Inspire2adventure, offer a range of SUP experiences for all ages and experience levels.
Just a 20-minute drive from Chepstow, you'll find the ethereal forest of Puzzlewood. Situated just over the Welsh border, this 14-acre ancient woodland offers meandering pathways and fantastical trees and is home to badgers, deer, foxes, rabbits, and bats. The spellbinding forest landscape is so enchanting that Kathleen Kennedy, President of Lucasfilm (known for the legendary Star Wars and Indiana Jones franchises), has even declared it "the most magical forest on the face of the earth".
It's easy to see why Puzzlewood has been a favourite location for filmmakers. Its surreal landscapes provide the perfect backdrop for productions like Merlin, Star Wars, and The Secret Garden (2020). The mysterious forest is a key filming location for Star Wars: The Force Awakens (2015). Producers transformed this ancient woodland into the lush, green forest world of Takodana where pivotal scenes unfold, including the dramatic lightsaber battle between Rey (Daisy Ridley) and Kylo Ren (Adam Driver). Puzzlewood's natural mystical atmosphere made it the perfect setting for this iconic scene. Star Wars location manager Martin Joy described the forest as "like nowhere else – it's an otherworldly space".
While Puzzlewood's natural beauty is undoubtedly its main draw, there's much more to discover beyond the twisting paths and ancient trees. Scattered throughout the forest are a series of intriguing features including bridges, lookouts, and even a few dead ends that add an element of mystery to your woodland exploration. Puzzlewood is also home to various animals, making it a delightful family destination. Visitors can meet Highland cattle, donkeys, ducks, and chickens, turning a walk through the woods into a mini safari. After exploring the forest, visitors can relax at the small takeaway café on site, which offers a range of refreshments. Alternatively, you can bring your own picnic and find a quiet spot in the woods to enjoy your feast surrounded by nature.
Food and drink in the Wye Valley
Foodie-wise, Chepstow is ideally positioned in the surprising gastro hotspot of the Wye Valley, where the lengthy River Severn meets the salmon-rich River Wye, carving through Wales and England. While this charming border area is known for its protected landscapes, ancient monuments, attractive market towns, and outdoor pursuits, it also has a thriving dining and foodie scene to discover. You can criss-cross seamlessly from Wales into England and easily explore the well-heeled area and its many restaurants, cafés, and producers.
Take a gastro-journey through the valley and you'll find locally-reared lamb, smoked eel, craft ales, and honey-infused mead. Local breweries include the small microbrewery Lydbrook Valley Brewing Company, which produces a 4.2% IPA, and the Wye Valley Brewery, which produces a decent range of craft ales. The Wye Valley is also home to White Castle Vineyard, where visitors can buy high-quality Welsh wines and take a tour.
Numerous pubs along the River Wye are a welcome rest spot if you're paddling up the river on an epic canoe or kayak trip while visiting Chepstow. The Boat Inn and the Anchor Inn 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. Their flagstone-floored bar and rustic pine tables provide a traditional pub feel as you sip on a pint of local real ale while watching the inn's ancient hand-ferry carry passengers across the Wye.
Over in the town centre, the Beaufort Hotel's award-winning restaurant offers guests a fabulous à la carte menu featuring traditional British and international dishes using Wye Valley and Welsh produce where possible. Tell me Wine is a wine merchant and French bistro lounge that offers delicious French dishes, wine tastings, and live music events. Family-owned Stone Rock Lodge serves Wales' best pizza, and you can get an excellent Sunday lunch at St Pierre. With one Michelin green star and four AA rosettes, dining at the Whitebrook is also a must for serious foodies. Fresh, local ingredients and foraged findings from the valley feature in the beautifully plated dishes at this highly acclaimed restaurant with rooms. Set in five acres of landscaped surroundings, chef Chris Harrod draws culinary inspiration from his bountiful surroundings. You can expect hand-foraged garlic, bittercress, wild onion, and hogweed from the valley, connecting diners to the immediate locale and enriching the carefully-crafted menu. The current tasting menu is a culinary journey, showcasing the best of the season with expertly chosen wine pairings of local Welsh and English wines, including several from Monmouthshire-based White Castle Vineyard.
Why not make a weekend of it and book a stay in the Whitebrook so you don't have to drive home after an incredible feast? They have eight rooms overlooking the Wye Valley and woodland. Rooms are individually designed and inspired by the natural surroundings outside. You'll find an impressive range of swish properties, guest houses, and hotels in Chepstow and the wider area to suit your travel style and budget. Airbnb and Booking.com have a range of unique stays in the Wye Valley, from bougie guest houses and cosy holiday cabins to luxury glamping and yurts. Further afield is the charming Tudor Farmhouse, which is around a 20-minute drive from Chepstow. This boutique hotel is a former working farm stylishly converted into a country getaway with rooms, cottages, and suites. Prices depend on the type of room booked.
