One of the many beautiful gateways to Wales, Chepstow promises an Arcadian adventure at the foot of the tree-tipped Wye Valley National Landscape. Nestled on the banks of the serene River Wye and boasting a pastiche of unique experiences and fascinating days out, this charming town invites you to luxuriate amidst rolling landscapes peppered with ancient landmarks and captivating pastimes.
Whether you long for a round of golf in a dappled wonderland or love nothing more than exploring romantic ruins for stories carved in stone, these unique experiences in Chepstow are sure to add magic to your bewitching sojourn.
Spend the day at Chepstow Racecourse
Home to Wales’ most prestigious races, Chepstow Racecourse invites you to don your Sunday finest for a day of thrilling spectatorship. The Coral Welsh Grand National has 30 meetings across the year, while events promise a unique experience amidst the spirited highs of the races, from country and western nights to ladies’ days. Stop by the restaurant for delectable dishes or book a private suite for an unrivalled day at the races.
Play a round at St Pierre Country Club
Set within the picturesque grounds of the St Pierre Country Club, there’s nowhere better to hone your golf skills. A medley of creative courses awaits, from the Old Course's challenging contours to the Signature Hole's waterside charms. When ready to refuel, head to the beautiful Cast Iron restaurant where verdant views and innovative menus await. Finally, unwind in the spa or book a luxury treatment to truly make the most of the historic offering. From facials to massages, St Pierre’s promises pampered moments in a blissful setting.
Step back in time at Tintern Abbey
The romantic ruins of Tintern Abbey beckon for a blissful day out beneath a rolling backdrop of wood-dusted hills and sprawling skies. Founded by Cistercian monks in the 12th century, the fascinating abbey has morphed over the years, evolving from a simple timber church to the Gothic masterpiece you see today. Picnic beneath the majestic arches and marvel at the time-worn ruins, explore the on-site exhibition for a glimpse into the past, and stop by the gift shop for fascinating guidebooks and charming mementoes.
Tour the ruins of Chepstow Castle
Perched atop the looming limestone cliffs with sprawling views across the shimmering waters of the River Wye, Chepstow Castle is one of the most unique places to visit in Chepstow and South Wales. Chepstow Castle was one of the first Norman strongholds in Wales, with the mighty fort boasting untold riches within its war-cracked walls, and a fascinating history of battles over 900 years is carved into the stone ruins. Today, marvel at the once mighty doors, trace the ancient walls, and pause on the battlements as you gaze across the wood-fringed river.
Explore the riverbanks of the Wye
Lined with ancient woodland that encompasses time-frayed landmarks and darling market towns and villages, the Wye Valley National Landscape (formerly known as an Area of Outstanding Natural Beauty) is a haven of leaf-strewn wonder perfect for exploring on foot or by water. Whether you adore the dappled delights of a riverside stroll or love nothing more than stepping into your very own watercraft for a day of whimsical adventures exploring hidden inlets and sun-soaked waterways, the River Wye is a dreamy way to take in the sights through the Wye Valley.
Trace the trails along Offa’s Dyke
Starting in the tranquil setting of Chepstow and ending in Liverpool Bay, the beloved Offa’s Dyke Path follows 177 miles of winding paths that often skirt the ancient earthwork known as Offa’s Dyke after the king who ordered its construction. Interlacing with the border between Wales and England, the ancient footpath promises a fascinating opportunity to walk in the footsteps of history as you uncover fascinating settlements and charming villages. Follow the trail for as long or as little as you desire, before returning to Chepstow to relish in the many beckoning restaurants.
Delve into the area’s past at Chepstow Museum
Set within an elegant 18th-century house with striking columns, Chepstow Museum invites you to explore Chepstow and the Wye Valley’s rich and varied history. Through time-tinted photographs and beautiful posters, paintings, and prints, you’ll quickly uncover why so many have been drawn to this tranquil corner of Wales. Exhibitions shift and change throughout the year, ensuring there’s always something new to capture your imagination.
Browse boutiques along the high street
Lined with an array of independent shops amidst beautiful Georgian and Victorian buildings, enjoying a little retail therapy is blissfully easy while staying in Chepstow. From jewellers and bookshops to antique shops that hide a treasure trove of finds behind the windowed doors, Chepstow’s picturesque high street promises a mesmerising montage of fascinating emporiums and boutiques. Dip into the Silver Circle distillery for an indulgent tasting or take a moment to soak up the otherworldly art in one of the art galleries.
Sup in style
Home to a medley of beloved restaurants, Chepstow boasts many epicurean experiences to indulge in while soaking up the idylls of South Wales. With Michelin restaurants on its doorstep and award-winning country pubs and restaurants tucked down the town’s winding streets, there’s something for every taste, whether you crave the fresh flavours of Mediterranean cuisine or soul-warming British classics. Book a table at The Whitebrook for Michelin star dining or sink into a riverside reverie at The Boat Inn.
Step onto the Wales Coast Path
Spanning 870 miles, the Wales Coast Path promises a salt-kissed adventure whenever the ocean calls. Beginning in Chepstow, take in sprawling views as you pass tranquil nature reserves and sun-soaked countryside parks, all while breathing in the refreshing sea air. Wildlife enthusiasts are invited to don their binoculars to see the resident wading birds and marine wildlife up close, while the shoreline promises serene picnics in a halcyon oasis.
Embark on dappled pursuits in the Forest of Dean
A sweeping patchwork of ancient pines and rustling oaks, the Forest of Dean is a magical destination to uncover while exploring the delights of Chepstow. Set between the River Wye, River Severn, Herefordshire, and Gloucester, this enchanting forest paints an otherworldly picture, with a diverse melange of animals calling the dappled depths home. Walkers will adore the winding paths that crisscross through the moss-strewn trees, while wildlife enthusiasts should head to Nagshead Nature Reserve for a menagerie of birdlife to spot.
Feeling inspired? Take a look at our luxury cottages in Wales.
