Car Hire Chepstow

Accessing Chepstow is remarkably straightforward thanks to its strategic position near major transport links. The M48 motorway connects you directly to Bristol (18 miles) and Cardiff (31 miles), while the A48 provides a scenic route towards Gloucester (29 miles) and the A466 leads north through the stunning Wye Valley to Monmouth. This historic town of approximately 11,900 residents experiences a temperate oceanic climate with comfortable summers reaching 16-20°C and mild winters hovering around 5-8°C, though you should prepare for frequent rainfall throughout the year and occasional strong Atlantic winds that can make temperatures feel cooler than expected.

Attractions In Chepstow

Discover medieval castle ruins and border town heritage, featuring impressive Norman fortifications, historic racecourse events, scenic river walks along the Wye and easy access to both Welsh and English countryside attractions.

Chepstow Castle

Bridge Street serves as home to one of Britain’s most significant medieval fortresses, where Chepstow Castle stands majestically above the River Wye. Operating daily from 10 AM until 4 PM, this remarkable structure boasts a 4.6-star rating from nearly 4,000 visitors. Construction began in 1067, making it amongst the oldest surviving stone castles in Britain and walking through its well-preserved gates transports you through centuries of military history while offering breathtaking views from the battlements.

Chepstow Port Wall

The medieval defences continue at Unnamed Road, where this historical landmark opens daily from 10 in the morning until 4 in the afternoon. This incredibly well-preserved section showcases Chepstow’s strategic importance during medieval times. The wall represents a tangible connection to the town’s past as a Norman stronghold, allowing you to trace the boundaries that once protected this crucial border settlement along the Welsh-English frontier.

Chepstow Town Gate

Standing proudly at 28-30 High Street, this impressive gateway tells the story of medieval urban planning and defence. Built between 1272 and 1278 by Roger Bigod III, Earl of Norfolk, it served dual purposes as both defensive structure and trade control point. The gate demonstrates remarkable preservation and remains open to locals and tourists alike, standing as a monument of national importance that enhances our understanding of medieval defensive architecture and urban development.

For convenient access to neighbouring areas, consider these popular destinations:

• Lydney
• Filton
• Newport
• Coleford
• Forest of Dean
• Wotton under Edge
• Dursley
• Kingswood

Naval Gun

High Street features this intriguing historical landmark that speaks to Chepstow’s maritime connections. This naval artillery piece, which originated from a submarine as a commemorative gift, represents the town’s relationship with Britain’s naval heritage. The display serves as a reminder of the broader military history that extends beyond the medieval fortifications, connecting Chepstow to more recent conflicts and Britain’s naval supremacy.

Churchyard Walk

The Priory Church of St Mary provides the setting for this historical pathway that appears on Millerd’s 1686 map. Traffic once flowed around the churchyard via Horse Lane, while pedestrians used the footpath through the church grounds. The elegant railings were installed between 1825-1827, with distinctive cast iron posts added in 1829, creating the refined Victorian character that defines this peaceful walk today.

Gloucester Hole

Located in Tutshill, this natural limestone cave was enlarged to create fascinating dimensions of 27 feet in both depth and breadth, reaching 15 feet in height. The entrance measures approximately 5 feet 6 inches square and extends about 12 feet into the rock. Adjacent to the cave, a Union Flag has been painted since 1935 to commemorate King George V’s Silver Jubilee, making this site both geological wonder and patriotic landmark.

Chepstow Cenotaph

High Street hosts this moving memorial, accessible five days weekly: Tuesdays, then Wednesday through Sunday from 11 AM until 4 PM. The monument features a two-stepped base supporting a tapering square column with sunken panels and fluted sides, crowned by an urn. Stone-carved inscriptions and three bronze plaques honour those who served, with two dedicated to First World War casualties and one commemorating Second World War heroes.

Priory Church Of St Mary

Upper Church Street houses this magnificent 11th-century Norman Priory featuring an original Romanesque doorway and nave. Open daily, the church contains the tombs of the Earl of Worcester and his wife Elizabeth, who served as lady-in-waiting to Anne Boleyn. You’ll discover Henry Marten’s tomb near the great west door, close friend of Oliver Cromwell and signatory to Charles I’s death warrant, alongside beautiful Victorian chancel restoration and Georgian tower bells.

Chepstow Museum

Bridge Street’s Gwy House welcomes visitors on Tuesdays and Thursday through Sunday from 11 in the morning until 4 in the afternoon. This heritage museum occupies a beautiful 18th-century townhouse that has served as both hospital and school throughout its history. The thoughtfully curated exhibits showcase Chepstow’s fascinating evolution from Norman stronghold to bustling Georgian port, offering families interactive experiences with craft activities and hands-on artefacts, all available free of charge.

Tidenham Tunnel

At Kinley Barn on Bishton Lane, this remarkable tunnel operates every day from 8 in the morning until 6 in the evening. Forming part of the trail connecting Chepstow to Tintern, the 1.5-kilometre tunnel offers a unique walking experience. The total 7-kilometre route provides excellent opportunities for countryside exploration, though the low lighting requires careful navigation along the left-hand side, making it perfect for adventurous day trips to Tintern.

Giant’s Cave

St Arvans provides year-round access to this spectacular natural attraction that offers brilliant views across the surrounding landscape. The walking route from Lower Wyndcliff car park presents some challenging sections with narrow paths and steep drops, requiring concentration and proper footwear. An alternative, easier access path leads from the main A466 road between the Piercefield pub and Wyes Cats luxury cat hotel, making this geological wonder accessible to different fitness levels.

Eagle’s Nest Viewpoint

Wyndcliffe Court offers this stunning scenic spot that remains available for tourists throughout the year, providing exceptional perspectives across the Wye Valley. This viewpoint ranks among the best along the entire Wye Valley, with access via Upper Wyndcliff car park eliminating the steepest climbing sections. The moderate route and 365-step descent option cater to different preferences, while the long bench provides perfect positioning for taking in the magnificent views across the River Wye and distant landscapes.

Piercefield Park

Hardwick Avenue leads to this exceptional park and garden that stands as Chepstow’s finest green space. The venue has welcomed various events including horse racing and tribute performances, with helpful staff consistently providing excellent service. The park’s elegant design and maintained gardens create an atmosphere that combines recreational opportunities with historical significance, making it popular for both casual visits and special occasions throughout the year.

Chepstow Riverside

Located along the River Wye banks, this remarkable park offers friends and families wonderful opportunities to enjoy Wales’ natural beauty and peaceful surroundings. The riverside setting provides excellent views and includes a bandstand that occasionally hosts musical performances. While jet skiing activities can sometimes interrupt the tranquillity, the park’s historical significance and scenic location make it a valuable green space for relaxation and outdoor activities, connecting visitors directly with the river’s natural environment.