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You are here: Explore Monmouthshire > Chepstow > Must-do Chepstow

Must-do Chepstow

Chepstow is a town made for exploring with plenty of things to do. Chepstow Castle towers over the River Wye, and is a great sight for those embarking on long distance walks such as the Wye Valley Walk, Wales Coast Path and Offa's Dyke Path. Then there's the fun of the races at Chepstow Racecourse, 1000 years of history at Chepstow Museum, beautiful views through Piercefield Park and much more to do in Chepstow.

Highlights and attractions in Chepstow

Inspiration

Chepstow Castle (Cadw)

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.
1. 1st Sept 202631st Oct 2026
2. 1st Nov 202631st Dec 2026
3. 1st July 202731st Aug 2027
Chepstow Museum

Chepstow Museum reveals the rich and varied past of this ancient town, once an important port and market centre. It's open 11am - 4pm every day except Monday and Wednesday.
1. 15th Feb 202622nd Dec 2026
Chepstow Racecourse

Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
1. 1st Jan 202631st Dec 2026
Walking in Chepstow
Chepstow events

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Chepstow Racecourse

Address

Chepstow Racecourse, Chepstow, Monmouthshire, NP16 6BE

Telephone
01291 622260

info@chepstow-racecourse.co.uk

Chepstow

Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
Chepstow Bridge - Old Wye Bridge

Address

Chepstow Bridge, Bridge Street, Chepstow, Monmouthshire, NP16 5EZ

Chepstow

Chepstow Bridge is the World's largest iron arch road bridge from the first 50 years (1780-1830) of iron and steel construction.
Captivate Gallery

Address

11 St Mary Street, Chepstow, Monmouthshire, NP16 5EW

Telephone
07595719524

steph@captivate-art.co.uk

Chepstow

Visit Captivate Gallery at 11 St Mary’s Street—stop by to say hello, enjoy local art, and mingle in a welcoming, dog-friendly atmosphere!
Chepstow Castle (Cadw)

Address

Chepstow Castle, Chepstow, Monmouthshire, NP16 5EY

Telephone
03000 252239

ChepstowCastle@gov.wales

Chepstow

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…
Health Walk - St. Arvan's Walk

Address

St Arvans Memorial Hall, A466,, St Arvans, Chepstow, Monmouthshire, NP16 6DN

Telephone
01633 644850

countryside@monmouthshire.gov.uk

St Arvans, Chepstow

2.8 mile route through and to the west of the village of St. Arvan's.
Eagle's Nest Viewpoint & Wyndcliff Wood

Address

Lower Wyndcliffe Car Park, St Arvans, Chepstow, Monmouthshire, NP16 6HA

Telephone
0300 065 3000

enquiries@naturalresourceswales.gov.uk

Chepstow

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.
Wyndcliffe Court House & Garden School

Address

Wyndcliffe Court House & Garden School, Wyndcliffe Court, St. Arvan's, Chepstow, Monmouthshire, NP16 6EY

Telephone
01291 630027

sarah@wyndcliffecourt.com

St. 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.
Chepstow Leisure Centre

Address

Welsh Street, Chepstow, Monmouthshire, NP16 5LX

Telephone
01291 635745

chepstowleisurecentre@monmouthshire.gov.uk

Chepstow

Visit Chepstow Leisure Centre to swim, play sports, keep fit and more.
Warren Slade and Park Redding Woods

Address

Thornwell, Chepstow, Monmouthshire, NP16 5TF

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

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.
Chepstow Town Trails

Address

Chepstow TIC, Bridge Street, Chepstow, Monmouthshire, NP16 5EY

Telephone
01291 623772

chepstow.tic@monmouthshire.gov.uk

Chepstow

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…
Chepstow Park Wood

Address

Devauden Road, Devauden, Monmouthshire, NP16 6EZ

Devauden

Chepstow Park Wood is an old medieval hunting park, created by the Norman lords of Chepstow Castle.
St. Arvan's Church

Address

St. Arvan's Church, Church Lane, St Arvans,, Chepstow, Monmouthshire, NP16 6EU

Telephone
01291 622064

frmichaelgollop1@gmail.com

St Arvans,, Chepstow

Medieval parish church of potential ninth century Celtic origin, named after the 9th century hermit St. Arvan.
The Giant's Cave Viewpoint

Address

St Arvans, Chepstow, Monmouthshire, NP16 6EG

Telephone
01600 710846

information@wyevalleyaonb.org.uk

Chepstow

The Giant's Cave is a dramatic viewpoint along the Wye Valley Walk north of Chepstow.
Walking or Cycling across the Severn Bridge

Address

The Severn Bridge, Chepstow, Monmouthshire, NP16 5AA

Chepstow

Walk or cycle across the (old) Severn Bridge along the M48 on this just under 5 mile route. It's a great way to experience the Severn Estuary, and to visit two countries in one walk.
Severnvale Equestrian Centre

Address

Tidenham, Chepstow, Monmouthshire, NP16 7LL

Telephone
01291 623412

svec@clara.co.uk

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.
Stone Rock Lodge - Sauna & Plunge

Address

Stone Rock Lodge, Upper Church Street, Chepstow, Monmouthshire, NP16 5EX

Telephone
01291 622189

Chepstow

A haven in the heart of Chepstow - indulge, refresh, and start your adventure.
Tourism For All

Chepstow Tourist Information Centre (TIC)

Address

Chepstow TIC, Castle Car Park, Chepstow, Monmouthshire, NP16 5EY

Telephone
01291 623772

chepstow.tic@monmouthshire.gov.uk

Chepstow

Chepstow TIC provides information on attractions, activities and events in the area as well as offering advice and help on booking accommodation.
5 St Arvans Roundabout

Address

St Arvans Memorial Hall, A466, St Arvans, Chepstow, Monmouthshire, NP16 6DN

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

A 5.4 mile hilly walk around the community of St Arvans north of Chepstow.
Woodhaven

Address

Woodhaven, Itton, Chepstow, Monmouthshire, NP16 6BX

Telephone
01291 641219

lesley@classics.co.uk

Chepstow

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.
St. Mary's Priory, Chepstow

Address

St Mary's Priory, Upper Church St, Chepstow, Monmouthshire, NP16 5HU

Telephone
01594 530080

hillnoramay@aol.com

Chepstow

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.