Things to do in Chepstow

UB40 ft. Ali Campbell Live After Racing Chepstow Racecourse

On Friday 24th July the legendary UB40 ft. Ali Campbell will be bringing all the reggae vibes as part of the annual Rum and Reggae night at Chepstow Racecourse.

Chepstow Racecourse, Chepstow

Super popular

Jools Holland and His Rhythm & Blues Orchestra

As ever, Jools continues to dazzle, involve and impress audiences with his Rhythm & Blues Orchestra and their exuberant live performances on their Jools Holland…

CADW: Chepstow Castle, Chepstow

Super popular

Wishbone Ash

Over 50 years of continual touring and recording It’s a remarkable milestone few bands have achieved… and always at the highest level.Discover for yourself why…

CADW: Chepstow Castle, Chepstow

Emilio Santoro as Elvis

Crowned ‘2024 Ultimate Elvis Tribute Artist World Champion’ by Elvis Presley Enterprises at Graceland, Emilio Santoro brings his award-winning Elvis Presley sho…

CADW: Chepstow Castle, Chepstow

Jools Holland's Boogie Woogie & Blues Spectacular

Jools hosts a piano pounding extravaganza featuring his choice of world class kings of the keyboard.There'll also be an array of special guests and accompanying…

CADW: Chepstow Castle, Chepstow

Circu5 at Summer's End Festival

Circu5 will perform on Sunday 18 October at Summer's End Festival. Other acts include Threshold, Landmarq, Held By Trees and Splink.

The Drill Hall, Chepstow

Chube / Dave Jones Stratospheric

A double-header featuring Chube and Dave Jones Stratospheric. Both bands have their own unique type of fusion - Chube are an electro acoustic trio utilising an…

The Drill Hall, Chepstow

SheKoyokh

General admission 20; Wye Valley Music members 17; 25 and under 2; 14 and under free.

The Drill Hall, Chepstow

The Big Brockweir Summer Party 2026

Building on the incredible magic of the last two years, were turning up the heat for 2026!This year, were channeling the spirit of the Summer of Love for our ve…

Mackenzie Hall, Chepstow

Romeo & Juliet - Chepstow Castle

Two hearts. One fate. A timeless love reborn. The Dukes Theatre Company presents Shakespeares Romeo and Juliet, a bold reimagining of the iconic tragedy directe…

CADW: Chepstow Castle, Chepstow

2Rude - The Small Fakers - A Band Called Malice

2rude - The ultimate SKA tribute For most ska fans 1980 had to be the year. The music of The Specials along with Madness, The Beat, The Selecter and Bad Manners…

CADW: Chepstow Castle, Chepstow

As December Falls & Guests

Line up : As December Falls Lake Malice Tigress Celavi As December Falls is an UK alternative/ emo rock band fighting against the tide of a change in the rock s…

CADW: Chepstow Castle, Chepstow

The Ultimate Eagles

Experience the most comprehensive and accurate homage to Eagles you are ever likely to hear from a world-class band.In just four short years, Ultimate Eagles ha…

CADW: Chepstow Castle, Chepstow

The Legends Series

This stunning replica live music concert show of three Legendary Bands is must-see.

CADW: Chepstow Castle, Chepstow

Scarlet Rebels

Scarlet Rebels are a five-piece Welsh melodic rock band residing in Llanelli, South Wales.

CADW: Chepstow Castle, Chepstow

The UK Monsters of Rock

The UK Monsters of Rock show will transport you back to the 80s heyday of classic rock, combining the feel of a rock festival with the atmosphere of a top end r…

CADW: Chepstow Castle, Chepstow

Experience the Beatles at Chepstow Drill Hall

Step back in time with Experience the Beatles South Wales freshest tribute to the Beatles, powered by raw talent and unstoppable energy.

The Drill Hall, Chepstow

Dick Whittington - Chepstow 2026

Lemon Jelly Pantos presents the PURR-FECT family pantomime, Dick Whittington, featuring all the traditional pantomime ingredients, with a multi-talented cast, t…

The Drill Hall, Chepstow