A guide to Chepstow: Where to eat, stay and visit

PUBLISHED: 12:40 10 June 2015 | UPDATED: 17:26 03 July 2015

Chepstow Castle

Chepstow Castle

(C) 2006 Hemera Technologies

The Countrywide Great Tour begins on 4 July 2015 and takes place over 64 days visiting numerous coastal and riverside locations across the UK, including Chepstow.

The map showing the route of Stage 55 - Chepstow to CardiffThe map showing the route of Stage 55 - Chepstow to Cardiff

On August 26, during the tour’s final stages, the Tour crosses back into Wales and stops overnight in the medieval town of Chepstow.

Now firmly in the hands of the Welsh, Chepstow, a riverside town situated by the River Wye with a dramatic history, is a border town that wears its history proudly

Here those supporting the cyclists, along with the early finishers, can spend hours exploring all the charms, and quaint narrow streets of this historic town, dominated by its Norman Castle. Built by William FitzOsbern in 1067, a close relative and friend of William the Conqueror, the castle would prove to be of huge strategic importance and help prevent the Welsh from invading Gloucestershire.

The Castle is now open to the public, and its grounds, with views over the town, make it the perfect place to picnic and await the cyclists return.

Visitors can learn more about the town’s history from its museum that charts the town’s journey from an ancient Norman battlement to a thriving market town.

While garden fans will love the Grade II listed Wyndcliffe Court Gardens, designed in the Arts and Crafts style, situated just outside Chepstow.

Chepstow is particularly famous as the home of the Welsh Grand National, which is run in the grounds of Piercefield House, a largely ruined neo-classical country house designed by the renowned architect Sir John Soane.

Did you know Harry Potter author J.K. Rowling attended Wyedean School and College in Chepstow?

Where to eat

The Riverside Wine Bar

Idyllically situated beside the River Wye, it is the perfect place to enjoy a drink or a bite to eat, especially after a hard day’s cycling. The menu includes light bites and tapas, paella, burritos and more… On Friday night it stops serving food at 10pm.


Those that like Asian food should check out Shangri-La, situated on St. Mary Street.

The menu is based around Chinese, Malaysian, Thai, Singaporean and Japanese cuisines.

Where to stay

St Pierre Marriott Hotel & Country Club

Close to Chepstow Castle and Chepstow Racecourse, the hotel’s facilities include a golf course, indoor and outdoor swimming pools fitness centre, a sauna, 2 restaurants and 2 bars/lounges.

Castle View Hotel

Dating back to the 17th century, this charming hotel dates back to the 17th century and, as its name suggests, overlooks the castle. It has been given three stars by the AA and the restaurant serves British cuisine with a little European influence.

Do you want to take part in the Great tour? To enter, head over to the Countrywide Great Tour website.

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