Rusty Shackle - Caldicot Castle

Caldicot Castle & Country Park 29 Aug 2026

The Big Banquet

Caldicot Castle, Church Rd, Caldicot NP26 4HU, NP264HU 22 May 2026

Dr John Cooper Clarke with special guest Mike Garry

Blake Theatre Monmouth 30 Apr 2026

South Wales Car Festival 2026

Chepstow Racecourse 3 May 2026

The Everything ELVIS Weekend Chepstow celebrates the music & legacy of Elvis Presley

Chepstow Town Centre 20 Jun 2026

Phil Campbell & The Bastard Sons - Chepstow Castle

Bridge St, Chepstow NP16 5EY 22 Aug 2026

MABON

Caldicot Castle, Church Rd, Caldicot NP26 4HU 25 Sep 2026

As December Falls, Lake Malice, Tigress in

Chepstow Castle 15 Aug 2026

Wye Valley Tunnel Run 19th July 2026

Wyedean School 19 Jul 2026

ABCM + SMALL FAKERS + 2RUDE // CHEPSTOW CASTLE

Castell Roc - Chepstows Friendly Festival 14 Aug 2026

Chepstow Spring Vegan Market 2026

Chepstow High Street 19 Apr 2026

Scarlet Rebels & Friends

Bridge St, Chepstow NP16 5EY 21 Aug 2026

Medieval Music Day - Chepstow Castle

Chepstow Castle 20 Jun 2026

Soul & Sage at the Racecourse

Chepstow Racecourse 18 Jul 2026

Scarlet Rebels headline Chepstow Castle

Chepstow Castle 21 Aug 2026

Chepstow Classic Car Show Plus Auto Jumble & Collector's Fair

Chepstow Racecourse 26 Apr 2026

Caldicot Street Food Festival Series 2026

43 Newport Road, NP26 4BQ Caldicot, United Kingdom 19 Jun 2026

A Vivaldi & Mozart Candlelight Experience In Chepstow🕯️Friday 3rd July

St Mary’s Church, Chepstow 3 Jul 2026

Hebogyddiaeth Canoloesol / Medieval Falconry🦅

Bridge Street, NP16 5EY Chepstow, United Kingdom 4 Apr 2026

Chepstow Summer Vegan Market

High Street, Chepstow, NP16 5, United Kingdom 30 Aug 2026