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 July 202531st Aug 2025
    2. 1st Sept 202531st Oct 2025
    3. 1st Nov 202531st Dec 2025
  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 202522nd Dec 2025
  3. Jockeys at Chepstow Racecourse
    Chepstow Racecourse has it all - beautiful countryside, a friendly charming atmosphere, and an impressive racing pedigree.
    1. 1st Jan 202531st Dec 2025

Number of results: 28

, currently showing 21 to 28.

  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

    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

  3. Address

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

    Telephone

    01291 625981

    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

  4. 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

  5. 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

  6. Address

    St. Arvans, Chepstow, Monmouthshire, NP16 6EG

    Telephone

    01600 740600

    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.

    Add Piercefield Woods Nature Reserve to your Itinerary

  7. 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

  8. 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

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