My Planner
My Planner
To build your own Itinerary, click 
to add an item to your Itinerary basket.
Already saved an Itinerary?
Highlights and attractions in Chepstow
Inspiration
Chepstow Castle is a must-visit as the oldest post-Roman stone castle in the UK (with the oldest castle doors in Europe!). It is a beautifully preserved masterpiece of medieval engineering, perched high above the Wye Valley like a history lesson in stone.- 1st July 202531st Aug 2025
- 1st Sept 202531st Oct 2025
- 1st Nov 202531st Dec 2025
- Chepstow Museum reveals the rich and varied past of this ancient town, once an important port and market centre. It's open 11am - 4pm. What3Words:- nimbly.magazines.acted
- 10th Feb 202522nd Dec 2025
- Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
- 1st Jan 202531st Dec 2025
Number of results: 27
, currently showing 1 to 20.
Address
Thornwell, Chepstow, Monmouthshire, NP16 5TFTelephone
01633 644850Chepstow
Woodland in Thornwell on the southeast edge of Chepstow. With dramatic views on top of cliffs at the lower end of The River Wye Gorge at Chepstow.
Address
Welsh Street, Chepstow, Monmouthshire, NP16 5LXTelephone
01291 635745Chepstow
Visit Chepstow Leisure Centre to swim, play sports, keep fit and more.
Address
St Arvans Memorial Hall, A466,, St Arvans, Chepstow, Monmouthshire, NP16 6DNTelephone
01633 644850St Arvans, Chepstow
2.8 mile route through and to the west of the village of St. Arvan's.
Address
Severn Bridge Social Club, Bulwark Rd, Bulwark, Chepstow, Monmouthshire, NP16 5JNTelephone
01633 644850Bulwark, Chepstow
2.6 miles around the Bulwark area of Chepstow, taking in the Wales Coast Path through Warren Slade.
Chepstow
Severnvale is British Horse Society Approved and carries out British Eventing Accredited training. It was selected by Horse & Hound’s Total Horse magazine, as one of the 10 best riding schools and training centres in the UK.
Chepstow
Celtic Trails want to give you the best walking holiday in Britain you can have. Your walking holiday will take you along the very best of National Trails and Long-Distance paths through Wales.
Tourism For All
Address
Chepstow TIC, Castle Car Park, Chepstow, Monmouthshire, NP16 5EYTelephone
01291 623772Chepstow
Chepstow TIC provides information on attractions, activities and events in the area as well as offering advice and help on booking accommodation.
Chepstow
Piercefield woods are the gateway to the Lower Wye Valley, stretching for over 3km along the river from near Chepstow castle in the south to Wyndcliff woods and the Eagle’s Nest in the North.
Address
Lower Church St, Chepstow, Monmouthshire, NP16 5HJTelephone
07526 445195Chepstow
The Drill Hall Chepstow is a community and arts venue in Chepstow.
Address
Chepstow Castle, Chepstow, Monmouthshire, NP16 5EYTelephone
03000 252239Chepstow
Chepstow Castle is a must-visit as the oldest post-Roman stone castle in the UK (with the oldest castle doors in Europe!). It is a beautifully preserved masterpiece of medieval engineering, perched high above the Wye Valley like a history lesson in…
Address
Chepstow Racecourse, Chepstow, Monmouthshire, NP16 6BETelephone
01291 622260Chepstow
Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
Address
Lower Wyndcliffe Car Park, St Arvans, Chepstow, Monmouthshire, NP16 6HATelephone
0300 065 3000Chepstow
Wyndcliff Wood is a superb example of a lower Wye Valley gorge woodland with ancient hanging beech and yew as well as lime, ash and hazel coppice.
Address
Woodhaven, Itton, Chepstow, Monmouthshire, NP16 6BXTelephone
01291 641219Chepstow
A modern house built on the site of a former sawmills for the Itton Court Estate. Garden of ⅔ of an acre developed over the last 20 years for year-round colour and interest.
Address
Veddw House, The Fedw, Devauden, Monmouthshire, NP16 6PHTelephone
01291 650836Devauden
Located deep in the heart of Monmouthshire, Veddw House Garden has been created through more than 20 years of patient work by Anne Wareham and Charles Hawes.
Chepstow
Celtic Trails want to give you the best walking holiday in Britain you can have. Your walking holiday will take you along the very best of National Trails and Long-Distance paths through Wales
Address
St Mary's Priory, Upper Church St, Chepstow, Monmouthshire, NP16 5HUTelephone
01594 530080Chepstow
St Mary's Priory has been a centre for prayer and worship for over 950 years. St Mary's Priory is open each day as a blessing to the community. Please feel free to enter and just be.
Address
St. Arvan's Church, Church Lane, St Arvans,, Chepstow, Monmouthshire, NP16 6EUTelephone
01291 622064St Arvans,, Chepstow
Medieval parish church of potential ninth century Celtic origin, named after the 9th century hermit St. Arvan.
Address
Mathern Road near Millers Arms, Mathern, Chepstow, Monmouthshire, NP16 6JDTelephone
01633 644850Chepstow
A 2.8 mile circuit in farmland between Mathern village and Chepstow.
Address
Chepstow TIC, Bridge Street, Chepstow, Monmouthshire, NP16 5EYTelephone
01291 623772Chepstow
Chepstow has three town trails. All start / finish at Chepstow TIC in the Castle car park, but you can pick them up at any point in the town centre. The full trail takes approximately 90 minutes. Look out for plaques of information in pavements and…
Address
Wyndcliffe Court House & Garden School, Wyndcliffe Court, St. Arvan's, Chepstow, Monmouthshire, NP16 6EYTelephone
01291 630027St. Arvan's, Chepstow
Anthony and Sarah Clay are thrilled to welcome garden visitors.
Wyndcliffe Court House and Garden School is held in the Edwardian Motor House recently converted into a lecture hall for informative talks and demonstrations.
Don't Miss
Don't Miss
Don't Miss
Don't Miss
Don't Miss
Don't Miss
© Visit Monmouthshire 2025. All Rights Reserved
