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Holidays in Chepstow

A peaceful riverside town on the Welsh border

UK | Wales | South Wales | Chepstow
Chepstow Castle

At a dramatic bend in the River Wye sits the walled market town of Chepstow, best known for being home to one of the UK’s best racecourses.

Chepstow is located in the Welsh county of Monmouthshire, right on the English border, 18 miles northwest from Bristol. As you approach the town, the first landmarks you’re likely to notice are the towering Chepstow Castle and the elegant bridge over the Wye, which dates back to the 1800s. Perched on a cliff, overlooking the town, the castle is considered to be one of the oldest remaining stone castles in Britain. During the Middle Ages, the port of Chepstow thrived as an importer of wine and an exporter of wood and bark from the nearby Wye Valley.

Chepstow Races by Amanda Slater - CC BY-SA 2.0

Chepstow hosts a number of exciting annual events, including Chepstow Festival, Hoggin’ the Bridge and the Welsh Grand National at Chepstow Racecourse. Chepstow Festival takes place from June 19 to July 25 and features theatre performances at the grounds of the castle. Hoggin’ the Bridge is a lively motorcycle rally which takes place in October and sees hundreds of bikers make their way from the magnificent Severn Bridge to Chepstow Racecourse.

For many, the biggest event in the town’s calendar is the Welsh Grand National, which attracts thousands of spectators and top jockeys, battling it out for the £120,000 prize.

Chepstow has a wide variety of places to eat and drink, from traditional tearooms and cafes to award-winning restaurants and historic pubs.

“At a dramatic bend in the River Wye sits the walled market town of Chepstow, best known for being home to one of the UK’s best racecourses.”

One of the town’s most popular spots for heart breakfasts, bacon rolls and sandwiches is Firstclass, a very reasonably priced café, right by the train station. For good coffee, homemade cakes and savoury snacks, check out Beveridge & Co, a relaxed café which is a hit with locals for its excellent service and consistently high quality. Alternatively, head to The Riverside Wine Bar for cocktails, wine and tapas with a view of the River Wye.

Take a look at our Chepstow cottages for more holiday inspiration.

While you’re there

Chepstow Museum

An interesting museum which tells the many stories of this ancient town's past

Chepstow Racecourse

Place a bet and cheer on your favourite horse at one of the many races during the year

Chepstow Castle

Enjoy the views from the oldest surviving stone castle in the UK

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