Chepstow trip planner
Create a fully customized
day-by-day itinerary for free
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, east-northeast of Cardiff, northwest 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.Chepstow is in Monmouthshire. Explore the family-friendly attractions of Chepstow and add them to your vacation plans using our United Kingdom trip itinerary maker tool .
Create a full itinerary — for free!
Plan your trip to Chepstow
Get a personalized planA complete day-by-day itinerary
based on your preferences
Customize itRefine your plan. We'll find the
best routes and schedules
Book itChoose from the best hotels
and activities. Up to 50% off
Manage itEverything in one place.
Everyone on the same page.
Top Chepstow tours
Cardiff 1-day tour Wye Valley BOOK WITH VIATOR FROM $57
Duration: 8 hours
Private South Wales Day Trip from Bath BOOK WITH VIATOR FROM $376
Duration: 9 hours
Cotswold Discovery Tour From Bath BOOK WITH VIATOR FROM $48
Duration: 7 to 9 hours
View all >
Side trips from Chepstow
Hidden gems in Chepstow
Historic Sites in Chepstow
Fun & Games in Chepstow
Outdoors in Chepstow
Places to visit with Chepstow
Recently planned trips to Chepstow
3 days in Chepstow BY A USER FROM UNITED KINGDOM July, popular sights PREFERENCES: July ATTRACTION STYLE: Popular sights PACE: Medium 3 days in Chepstow BY A USER FROM MALTA October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Chepstow BY A USER FROM UNITED KINGDOM August, outdoors, historic sites, museums, shopping, wildlife, slow & easy, hidden gems PREFERENCES: August, outdoors, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 11 days in Bristol & Chepstow BY A USER FROM THAILAND August, culture, romantic, historic sites, slow & easy, hidden gems PREFERENCES: August, culture, romantic, historic sites ATTRACTION STYLE: Hidden gems PACE: Slow & easy 1 day in Chepstow BY A USER FROM UNITED KINGDOM August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium 1 day in Chepstow BY A USER FROM FRANCE August, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Medium