GPS Cycle and Walking Routes

Chepstow Circular Walk

11 miles (18 km)

A splendid circular walk around Chepstow making use of the Wye Valley Walk and Offa's Dyke Path to visit some of the highlights of the area. There's lovely views of the River Wye, lots of peaceful woodland trails and a visit to the historic Tintern Abbey as you pass from Wales into England.
The walk starts at Chepstow Castle, the oldest surviving post-Roman stone fortification in Britain. From here you can pick up the Wye Valley Walk and follow it past the town before picking up woodland trails through Alcove Wood and Pierce Wood. You then pass Piercefield Park and Piercefield House,a largely ruinedneo-classicalcountry house dating from the late 18th century.
You continue past Chepstow Race Course, before climbing to the Eagle's Nest viewpoint on 365 steps trail. Here you will stand high above the Wye at Wyndcliff, looking out over the sweeping curve of the river around the Lancaut Peninsula.
The route then descends through Wyndcliff Wood and Black Cliff Wood before coming to Tintern Abbey. Here you can explore the fascinating ruins of a 12th century monastery. It's a beautiful area with the atmospheric ruins and the river flanked by the attractive woodland of the Forest of Dean.
After passing the abbey you cross the river on the old Tintern Railway Bridge which carried the Tintern Wireworks Branch trains over the river until 1935.
Heading south the next section picks up the Offa's Dyke Path and climbs to the viewpoint at the Devil's Pulpit. From here there are more wonderful views over the abbey and the AONB.
The route then continues to Plumweir Cliff and Worgan Wood before coming to the village of Woodcroft. Here you will pass Wintour's Leap where there are some magnificent limestone cliffs and Peregrine Falcons to look out for.
The final section takes you from Woodcroft back into Chepstow, crossing the river before returning to the castle.

Chepstow OS Map - Mobile GPS OS Map with Location tracking

Chepstow Open Street Map - Mobile GPS Map with Location tracking

Walks near Chepstow

  • Wye Valley Walk - This walk takes you through the beautiful Wye Valley in Gloucestershire, Herefordshire and Wales.
    The walk begins on the mouth of the River Wye at Chepstow Castle in Monmouthshire and follows the River Wye north to Monmouth, passing the fascinating ruins of Tintern Abbey on the way
  • Tintern Abbey - Visit the fascinating ruins of this 12th century monastery and then explore the surrounding area on this walk on the England-Wales border
  • Devil's Pulpit - Climb to this wonderful viewpoint and enjoy views over the Wye Valley AONB on this circular walk in Tintern in the Forest of Dean.
    You can start the walk from the car park off the B4228 just north of Tidenham
  • Wintour's Leap - Climb to this magnificent limestone viewpoint on this walk in the Wye Valley
  • Tintern Old Station - This park is situated in the Wye Valley Area of Outstanding Natural Beauty (AONB) near Chepstow
  • Chepstow Park Wood - This large area of woodland is located a few miles north west of Chepstow
  • Symonds Yat Rock - Enjoy wonderful views over the Wye Valley from this well known viewpoint on the Herefordshire and Gloucestershire border
  • The Kymin - Climb to the 245m (800ft) summit of Kymin Hill and enjoy wonderful views down the Wye Valley, up into the Brecon Beacons and across to the Malvern Hills
  • Monmouth - A lovely circular walk around the Welsh town of Monmouth, visting Monmouth Castle, The Kymin viewpoint and the River Wye
  • Severn Bridge - Cross from England into Wales on this walk across the Severn Bridge
  • King Arthurs Cave - This circular walk visits the mysterious King Arthur's Cave in the Wye Valley AONB near Symonds Yat
  • Wentwood Forest - Wentwood Forest is located a few miles north east of Newport in South Wales
  • St Briavels - This Gloucestershire based village sits close to the Welsh Border in the Forest of Dean and the River Wye Valley.
  • Caldicot Castle - This medieval castle is surrounded by a beautiful 55 acre country park with woodland, grassland and several walking paths.
  • Brockweir - This Gloucestershire based village sits in a beautiful spot in the Forest of Dean
  • Wye Valley Greenway - This cycling and walking route runs along a disused railway line through the beautiful Wye Valley.
  • Eagle's Nest - This walk takes you to the Eagle's Nest viewpoint in the Wye Valley AONB
  • Lancaut Walk - This walk explores the Lancaut Peninsula in the Wye Valley AONB

Further Information and Other Local Ideas

A few miles to the north east you could visit the interesting village of St Briavels. Here you will find the historic St Briavels Castle which dates back to the 12th century and is open to the public under the care of English Heritage. The village can be accessed by crossing the Bigsweir Bridge over the Wye from Llandogo in Wales to St Briavels in England on the other side. In Llandogo you can enjoy a walk to the pretty Cleddon Falls on the River Cleddon.
Near here there's Brockweir where there is easy access to the historic ruins of Tintern Abbey and Tintern Old Station, where you can learn all about the history of the local railway.
For more walking ideas in the area see the Forest of Dean Walks page.


Chepstow Castle, Chepstow

Chepstow Castle

Bridge over Wye - - 682946

Bridge over Wye

Wye Valley from Lower Wyndcliff Wood - - 122548

Piercefield House

The Wye Valley viewed from Eagle's Nest - - 801044

The Wye Valley viewed from Eagle's Nest

Wynd Cliff face (365 Steps) - - 543488

Wynd Cliff face (365 Steps)

View west from near Devil's Pulpit - - 812727

View west from near Devil's Pulpit

Tintern Abbey and Courtyard

Tintern Abbey and Courtyard

Offa's Dyke - Tidenham Section - - 167307

Offa's Dyke - Tidenham Section

GPS Files

GPX File

Chepstow.gpx (On Desktop:Right Click>Save As. On Ipad/Iphone:Click and hold>Download Linked File)

Memory Map Route

Chepstow.mmo (On Desktop:Right Click>Save As. On Ipad/Iphone:Click and hold >Download Linked File)