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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: 31

, currently showing 21 to 31.

  1. Address

    Tidenham, Chepstow, Monmouthshire, NP16 7LL

    Telephone

    01291 623412

    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.

    Add Severnvale Equestrian Centre to your Itinerary

  2. Address

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

    Telephone

    01291 622064

    St Arvans,, Chepstow

    Medieval parish church of potential ninth century Celtic origin, named after the 9th century hermit St. Arvan.

    Add St. Arvan's Church to your Itinerary

  3. Address

    St Arvans, Chepstow, Monmouthshire, NP16 6EG

    Telephone

    01600 710846

    Chepstow

    The Giant's Cave is a dramatic viewpoint along the Wye Valley Walk north of Chepstow.

    Add The Giant's Cave Viewpoint to your Itinerary

  4. 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

  5. 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

  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

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

    Telephone

    01633 644850

    Chepstow

    A 2.8 mile circuit in farmland between Mathern village and Chepstow.

    Add Health Walk - Mathern & Wyelands to your Itinerary

  8. 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

  9. 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

  10. 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

  11. Address

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

    Telephone

    0300 065 3000

    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.

    Add Eagle's Nest Viewpoint & Wyndcliff Wood to your Itinerary

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