Things To Do

Whether visiting for a day or staying as a base to explore the area,
Chepstow has something for everyone.


Chepstow Castle

Don’t miss the chance to visit the oldest surviving stone castle in Britain, the southernmost of a chain of castles along the Marches constructed to defend and control the border between England and Wales. Building was started in 1067 by Earl William fitz Osbern, close friend of William the Conqueror, making it one of the first Norman strongholds in Wales. The Castle has events throughout the year and a gift shop.


Chepstow Museum

The Museum is just across the road from Chepstow Castle in the 18th century Gwy House, built by a prosperous Chepstow merchant family. The wine trade, shipbuilding and salmon fishing are among Chepstow's many industries featured in displays. The Museum has a gift shop inside.


Chepstow Port Wall

The late 13th-century town walls of Chepstow were largely the work of Roger Bigod II, Earl of Norfolk. Bigod built strong stone walls around the town and linked them to Chepstow Castle. The River Wye and the castle protected the town to the north, and the Port Wall to the south.


St Mary’s Priory Church

Parts of the building, including its ornate west doorway, date from the late 11th century and are contemporary with the nearby castle. The church is a Grade I listed building as of 6 December 1950.

Among the tombs at St Mary’s is that of Elizabeth Browne (1500-1565). She married the Earl of Worcester and became a lady-in-waiting for Anne Boleyn, King Henry VIII’s wife. Also buried here is Henry Martyn, a close friend of Oliver Cromwell and a signatory to King Charles I’s death warrant.


Piercefield House

Take a walk up to Piercefield House, a largely ruined neo-classical country house near St Arvans, about 1.5 miles north of the centre of Chepstow. The central block of the house was designed in the very late 18th century, by, or to the designs of, Sir John Soane.

The house has an interesting history. In 1802, the estate was bought by Nathaniel Wells, son of William Wells, a slaver from Saint Kitts. Nathaniel received his freedom, inherited the bulk of his father’s wealth and went on to become a JP, Lieutenant in the Chepstow Yeomanry, as well as High Sheriff of Monmouthshire.


Town Trails

Town Trails

You can find out more about Chepstow and its history by walking the town trail.

Click the button below to download the map!


Poppy Trail

Click the button below to download more information on the Poppy Trail


Leisure & Events

Chepstow Racecourse

There has been horse racing in Chepstow for over 100 years. Chepstow Racecourse hosts 32 racing fixtures each year, including live music and family events. It is home to the prestigious Coral Welsh Grand National, as well as being available for hire (events, meetings and wedding receptions).


Silver Circle Shop and Tasting Room

Why not visit the Silver Circle Shop and Tasting Room. Silver Circle Distillery produce handmade craft spirits in the Monmouthshire village of Catbrook, deep in the Wye Valley Area Of Natural Beauty.

Located at 31 Moor Street, Chepstow NP16 5DD


Tell Me Wine

Fancy a wine and tapas tasting or dining experience? Contact Tell Me Wine, located in Nelson Street for more information and booking.


Castle Roc

Castell Roc is a family friendly, annual music festival, ranging from country and classical to rock.

Held during the summer, within the stunning Castle in Chepstow, praised and recognised for its relaxed and chilled out atmosphere. 


Play golf at St Pierre

The nearby St. Pierre Marriott Hotel & Country Club showcases two championship golf courses, in picturesque countryside, providing the ideal backdrop for a social gathering or business event.

The hotel and country club also offers spa facilities and breaks, including pool, whirlpool, steam and treatments. Afterwards, you can enjoy a delicious lunch or dinner in one of several hotel facilities.


Walking and Cycling

Chepstow is an ideal base for walking in Monmouthshire, the Wye Valley and Forest of Dean.

With such a diverse landscape there is everything to offer the walker and visitor whether it be a riverside stroll or a challenging walk along a long-distance trail. In April 2012, Chepstow became the first Walkers are Welcome town in Monmouthshire. The area was already established as a destination for walkers, with the Wales Coastal Path, Gloucestershire and Monmouthshire Ways and Offa’s Dyke. With the Walkers are Welcome status, it reinforces an ambition to provide the best walking experience for visitors and the local community alike. 


For further information on walking in the area:

Chepstow Walkers are Welcome
Chepstow Walkers are Welcome (


The Wales Coastal Path
Wales Coast Path


The Monmouthshire Way
The Monmouthshire Way


Gloucestershire Way
Gloucestershire Way - LDWA Long Distance Paths


Offa’s Dyke
Offa's Dyke Path National Trail - LDWA Long Distance Paths

With such a diverse landscape, Chepstow is also an ideal base for cycling within Monmouthshire and beyond. Further information can be found at:

Sustrans National Cycle Network
Home -


Visit the Severn Princess

Chepstow is home to the Severn Princess, the only ferry remaining from a group of 3 – the Severn King, Queen and Princess. These ferries carried vehicles and passengers across the river between Aust and Beachley, before the Severn Bridge was built. The Princess was launched in 1959, sold in 1966 but rescued from Ireland in a dreadful state and returned home to Chepstow in 1999.

It is currently undergoing restoration. Visits are currently by appointment only.



Why not take a walk along the beautiful riverbank looking out for seals and peregrines, stopping off for a drink and some delicious food at one of our pubs and restaurants nearby.