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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 July 202631st Aug 2026
    2. 1st Sept 202631st Oct 2026
    3. 1st Nov 202631st Dec 2026
  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: 32

, currently showing 21 to 32.

  1. Address

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

    Telephone

    01633 644850

    Chepstow

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

    Add 5 St Arvans Roundabout to your Itinerary

  2. 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

  3. Address

    Chepstow Castle, Chepstow, Monmouthshire, NP16 5EY

    Telephone

    03000 252239

    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…

    Indicative Availability

    Book Chepstow Castle (Cadw) Online (opens in a new window)

    Add Chepstow Castle (Cadw) to your Itinerary

  4. 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

  5. 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

  6. Address

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

    Telephone

    01633 644850

    Chepstow

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

    Add Health Walk - Piercefield Walk to your Itinerary

  7. 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

  8. Address

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

    Telephone

    07595719524

    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!

    Add Captivate Gallery to your Itinerary

  9. 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.

    Add Walking or Cycling across the Severn Bridge to your Itinerary

  10. Address

    The Severn Bridge, Chepstow, Monmouthshire, NP16 5AA

    Chepstow

    Severn Bridge parkrun is a free, fun, and friendly weekly 5k community event. Walk, jog, run, volunteer or spectate – it's up to you!

    Add Severn Bridge parkrun to your Itinerary

  11. 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.

    Add Chepstow Park Wood to your Itinerary

  12. Address

    Lower Church St, Chepstow, Monmouthshire, NP16 5HJ

    Telephone

    07526 445195

    Chepstow

    The Drill Hall Chepstow is a community and arts venue in Chepstow.

    Add The Drill Hall, Chepstow to your Itinerary

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