To provide you with the best experience, cookies are used on this site.  Learn more

Allow cookies

Must-do Chepstow

Highlights and attractions in Chepstow

Inspiration

  1. Chepstow Castle
    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 Nov 202631st Dec 2026
    2. 1st July 202731st Aug 2027
    3. 1st Sept 202731st Oct 2027
  2. 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
  3. Jockeys at Chepstow Racecourse
    Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
    1. 1st Jan 202631st Dec 2026

Number of results: 33

, currently showing 21 to 33.

  1. Address

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

    Telephone

    01291 630027

    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.

    Add Wyndcliffe Court House & Garden School to your Itinerary

  2. Address

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

    Telephone

    01594 530080

    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.

    Add St. Mary's Priory, Chepstow to your Itinerary

  3. Address

    Tintern, Chepstow, Monmouthshire, NP16 7ED

    Telephone

    01291 689774

    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

    Add Celtic Trails Walking - Offas Dyke Path to your Itinerary

  4. 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.

    Add Chepstow Bridge - Old Wye Bridge to your Itinerary

  5. Address

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

    Telephone

    01291 623772

    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…

    Add Chepstow Town Trails to your Itinerary

  6. Address

    Chepstow Racecourse, Chepstow, Monmouthshire, NP16 6BE

    Telephone

    01291 622260

    Chepstow

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

    Add Chepstow Racecourse to your Itinerary

  7. Tourism For All

    Self-Assessed Accessibility Information

    Address

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

    Telephone

    01291 623772

    Chepstow

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

    Add Chepstow Tourist Information Centre (TIC) to your Itinerary

  8. Address

    Shops Area, Thornwell Road, Thornwell, Chepstow, Monmouthshire, NP16 5TY

    Telephone

    01633 644850

    Chepstow

    3 mile walk around the countryside to the south west of Chepstow.

    Add Health Walk - Thornwell and Innage Walk to your Itinerary

  9. Address

    Delta Hotels by Marriott St Pierre Country Club, St Pierre Park, Chepstow, Monmouthshire, NP16 6YA

    Telephone

    01291 625261

    Chepstow

    Delta Hotels by Marriott St Pierre Country Club is built around a beautiful 14th Century Manor House set amidst 400 acres of tranquil parkland including two 18-hole golf courses.

    Add Golf at St Pierre Country Club to your Itinerary

  10. Address

    Wye Valley, Chepstow, Monmouthshire, NP16 6ZD

    Telephone

    01291 689774

    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.

    Add Celtic Trails - Wye Valley Walk to your Itinerary

  11. Address

    Thornwell, Chepstow, Monmouthshire, NP16 5TF

    Telephone

    01633 644850

    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.

    Add Warren Slade and Park Redding Woods to your Itinerary

  12. Tourism For All

    Self-Assessed Accessibility Information

    Address

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

    Telephone

    01291 625981

    Chepstow

    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.

    Add Chepstow Museum to your Itinerary

  13. Address

    Woodhaven, Itton, Chepstow, Monmouthshire, NP16 6BX

    Telephone

    01291 641219

    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.

    Add Woodhaven to your Itinerary

Don't Miss

Don't Miss

Don't Miss

Don't Miss

Don't Miss

Don't Miss

Don't Miss

  • Cymru Wales Logo
  • Site Logo
  • Monlife Logo
  • Monmouthshire Logo