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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 Nov 202531st Dec 2025
    2. 1st July 202631st Aug 2026
    3. 1st Sept 202631st Oct 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 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: 30

, currently showing 21 to 30.

  1. 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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 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

  7. 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

  8. Address

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

    Telephone

    01633 644850

    Bulwark, Chepstow

    2.6 miles around the Bulwark area of Chepstow, taking in the Wales Coast Path through Warren Slade.

    Add Health Walk - Bulwark Walk to your Itinerary

  9. 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

  10. 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

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