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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 July 202631st Aug 2026
2. 1st Sept 202631st Oct 2026
3. 1st Nov 202631st Dec 2026
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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Health Walk - Piercefield Walk

Address

Chepstow Leisure Centre, Welsh Street, Chepstow, Monmouthshire, NP16 5LT

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

2.6 mile route through Piercefield Park and returning on a section of the Wye Valley Walk.
Chepstow Bridge - Old Wye Bridge

Address

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

Telephone
01291 625981

chepstowmuseum@monmouthshire.gov.uk

Chepstow

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

Address

Veddw House, The Fedw, Devauden, Monmouthshire, NP16 6PH

Telephone
01291 650836

anne@veddw.co.uk

Devauden

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.
Health Walk - Mathern & St Pierre

Address

Mathern Road near Millers Arms, Mathern, Chepstow, Monmouthshire, NP16 6JD

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

2.7 miles from the village of Mathern, through farmland and the St Pierre golf course.
Tourism For All

Chepstow Tourist Information Centre

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.
Health Walk - Bulwark Walk

Address

Severn Bridge Social Club, Bulwark Rd, Bulwark, Chepstow, Monmouthshire, NP16 5JN

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Bulwark, Chepstow

2.6 miles around the Bulwark area of Chepstow, taking in the Wales Coast Path through Warren Slade.
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.
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 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…
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.
Health Walk - Mathern & Wyelands

Address

Mathern Road near Millers Arms, Mathern, Chepstow, Monmouthshire, NP16 6JD

Telephone
01633 644850

countryside@monmouthshire.gov.uk

Chepstow

A 2.8 mile circuit in farmland between Mathern village and Chepstow.
Celtic Trails - Wye Valley Walk

Address

Wye Valley, Chepstow, Monmouthshire, NP16 6ZD

Telephone
01291 689774

walk@celtic-trails.com

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.
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.
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.
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.
Piercefield Woods Nature Reserve

Address

St. Arvans, Chepstow, Monmouthshire, NP16 6EG

Telephone
01600 740600

info@gwentwildlife.org

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.
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.