©

Chepstow trip planner

Create a fully customized
day-by-day itinerary for free

Itinerary Planner
+ Add destination
2 adults
Adults
- +
Teens
- +
Kids
- +
Close

Chepstow

Trip Planner Europe  /  UK  /  Wales  /  South Wales  /  Monmouthshire  /  Chepstow
Historic Sites Adventure Museums
Chepstow is a town in Monmouthshire, Wales, adjoining the border with Gloucestershire, England. It is located on the River Wye, about above its confluence with the River Severn, and adjoining the western end of the Severn Bridge. It is east of Newport, north-west of Bristol and west of London.Chepstow Castle, situated on a clifftop above the Wye and its bridge, is often cited as the oldest surviving stone castle in Britain. The castle was established by William FitzOsbern immediately after the Norman conquest, and was extended in later centuries before becoming ruined after the Civil War. A Benedictine priory was also established within the walled town, which was the centre of the Marcher lordship of Striguil. The port of Chepstow became noted in the Middle Ages for its imports of wine, and also became a major centre for the export of timber and bark, from nearby woodland in the Wye valley and Forest of Dean. In the late eighteenth century the town was a focus of early tourism as part of the "Wye Tour", and the tourist industry remains important. Other important industries included shipbuilding – one of the First World War National Shipyards was established in the town – and heavy engineering, including the prefabrication of bridges and, now, wind turbine towers. Chepstow is also well known for its racecourse, which has hosted the Welsh National each year since 1949.
Find what you're looking for from your Chepstow holiday, by planning the whole thing with us using our handy United Kingdom (UK) vacation planner.
Source
Create a full itinerary — for free!

Plan your trip to Chepstow

  • Get a personalized plan

    A complete day-by-day itinerary
    based on your preferences
  • Customize it

    Refine your plan. We'll find the
    best routes and schedules
  • Book it

    Choose from the best hotels
    and activities. Up to 50% off
  • Manage it

    Everything in one place.
    Everyone on the same page.

Where to stay in Chepstow

Browse hundreds of hotels and read guest reviews on the world's leading online travel agency website.
CHECK IN - CHECK OUT
TripAdvisor
Millions of travel reviews
on TripAdvisor

Extend your holiday

Visit top cities near Chepstow:
Museums, sightseeing, spas
Visit for: 4 daysStart a plan »
Sightseeing, museums, historic sites
Visit for: 4 daysStart a plan »
Sightseeing, museums, nightlife
Visit for: 3 daysStart a plan »
Historic sites, museums, shopping
Visit for: 1 dayStart a plan »
Sightseeing, outdoors, beaches
Visit for: 1 dayStart a plan »

Recently planned trips to Chepstow

22 days in Wales BY A USER FROM UNITED KINGDOM August, kids, culture, outdoors, romantic, beaches, historic sites, museums, hidden gems PREFERENCES: August, kids, culture, outdoors, romantic, beaches, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Medium 5 days in Monmouthshire BY A USER FROM UNITED KINGDOM September, popular PREFERENCES: September ATTRACTION STYLE: Popular PACE: Medium 58 days in Middle East & Europe BY A USER FROM AUSTRALIA November, teens, kids, culture, outdoors, historic sites, museums, slow & easy, popular PREFERENCES: November, teens, kids, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular PACE: Slow & easy 58 days in Middle East & Europe BY A USER FROM AUSTRALIA November, teens, kids, culture, outdoors, historic sites, museums, slow & easy, popular PREFERENCES: November, teens, kids, culture, outdoors, historic sites, museums ATTRACTION STYLE: Popular PACE: Slow & easy 3 days in Chepstow BY A USER FROM UNITED KINGDOM July, teens, popular PREFERENCES: July, teens ATTRACTION STYLE: Popular PACE: Medium 6 days in United Kingdom BY A USER FROM UNITED STATES October, culture, relaxing, beaches, historic sites, museums, shopping, hidden gems PREFERENCES: October, culture, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 10 days in Wales BY A USER FROM CANADA October, culture, relaxing, historic sites, popular & hidden gems PREFERENCES: October, culture, relaxing, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Wales BY A USER FROM UNITED KINGDOM July, culture, outdoors, romantic, beaches, historic sites, shopping, hidden gems PREFERENCES: July, culture, outdoors, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 9 days in South Wales BY A USER FROM UNITED STATES October, culture, relaxing, historic sites, museums, hidden gems PREFERENCES: October, culture, relaxing, historic sites, museums ATTRACTION STYLE: Hidden gems PACE: Medium 10 days in Wales BY A USER FROM DENMARK July, culture, outdoors, relaxing, romantic, beaches, historic sites, popular & hidden gems PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 3 days in Monmouthshire BY A USER FROM UNITED KINGDOM July, outdoors, beaches, historic sites, shopping, popular PREFERENCES: July, outdoors, beaches, historic sites, shopping ATTRACTION STYLE: Popular PACE: Medium 38 days in United Kingdom, Dublin & Drogheda BY A USER FROM AUSTRALIA August, popular PREFERENCES: August ATTRACTION STYLE: Popular PACE: Medium
View more plans