Entertainment events in Caldicot

Check out happening entertainment events all around Caldicot, WA

Monster Truck Motorfest Chepstow

 Sat, 04 Jul at 10:00 am Chepstow Racecourse

The Big Banquet

 Fri, 22 May at 05:00 pm Caldicot Castle, Church Rd, Caldicot NP26 4HU, NP264HU

Rusty Shackle - Caldicot Castle

 Sat, 29 Aug at 04:30 pm Caldicot Castle & Country Park

Silva Bumpa, Omar+, Maya Jane Coles, bullet tooth, Murphy's Law (UK), Kepler., Locklead, Joss Dean, BSEARL, Cam Stockman, Laidlaw, Jack Gardner, Alexandria, Captain Wallop, Oldboy, Nay Barr, Manda Moor, Lucas Alexander, Julian Anthony, Reeshy, Trixie, Wheats, Jonny G, Ryan Nicholls, Dungeon Meat, Roberto in Monmouthshire

 Fri, 10 Jul at 01:00 pm Piercefield Park

Hayseed Dixie + The Zipheads

 Thu, 13 Aug at 06:30 pm Chepstow Castle, NP16 5EY Chepstow, United Kingdom

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

 Sat, 20 Jun at 06:00 pm Chepstow Town Centre

ABCM + SMALL FAKERS + 2RUDE // CHEPSTOW CASTLE

 Fri, 14 Aug at 06:30 pm Castell Roc - Chepstows Friendly Festival

Caldicot Street Food Festival Series 2026

 Fri, 19 Jun at 05:00 pm 43 Newport Road, NP26 4BQ Caldicot, United Kingdom

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

 Fri, 03 Jul at 06:00 pm St Mary’s Church, Chepstow

BASS ODDY - KIMFLUENCE DAYFEST

 Sat, 25 Jul at 02:00 pm The Lion - Chepstow

The Goodges Rock Out live @ The Five Alls, Chepstow. NP16 5ER.

 Fri, 12 Jun at 09:00 pm The Five Alls Inn Chepstow

ELVIS Gospel Show with Ben Thompson @ St Mary's Priory Church, Chepstow

 Sun, 21 Jun at 06:30 pm Priory Church of St Mary, Chepstow

James Maddock @ St James' Church

 Fri, 19 Jun at 06:45 pm St James The Great Devauden

A Taylor Swift Candlelight Experience In Chepstow - Friday 9th October

 Fri, 09 Oct at 06:00 pm St Mary’s Church, Chepstow

A Taylor Swift Candlelight Experience In Chepstow - Friday 6th November

 Fri, 06 Nov at 07:00 pm St Mary’s Church, Chepstow

The ELVIS Show @ The Drill Hall, Chepstow

 Sat, 20 Jun at 06:30 pm The Drill Hall Chepstow

As December Falls plus Guests

 Sat, 15 Aug at 07:00 pm Bridge St, Chepstow NP16 5EY

The Undercover Hippie - Solo Tour / 14th August

Fri, 14 Aug at 08:30 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

Castell Roc, Chepstow Castle

 Sun, 16 Aug at 07:30 pm Castle Wood, Chepstow, NP16 5, United Kingdom

An Evening with Maggie Aderin

 Sat, 27 Jun at 07:00 pm Blake Theatre Monmouth

MAN THE LIFEBOATS- Friday 5th June

 Fri, 05 Jun at 08:30 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

Steampunk Family Fun Day - Caldicot Town Centre

 Fri, 24 Jul at 10:00 am 43 Newport Road, NP26 4BQ Caldicot, United Kingdom

David Hanratty & His Band and Special Guest

Fri, 29 May at 07:30 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

Bouncing Dragons 2026 Annual Funday

 Sat, 15 Aug at 10:00 am The Measure inn

CMVC Summer Concert

 Sat, 06 Jun at 07:00 pm Priory Church of St Mary, Chepstow

Els Errorets- Free live music at Chepstow Art Space

Fri, 12 Jun at 08:30 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

Midweek Musical Bingo at Pontio Lounge (Chepstow) - Tuesday 16th June 7pm

 Tue, 16 Jun at 07:00 pm Pontio Lounge

The return of Rewind, a night of Kisstory classics

 Sat, 27 Jun at 09:00 pm The Lion - Chepstow

Ben Nicholls: Live at The Boat Inn, Chepstow

 Sat, 20 Jun at 03:30 pm The Boat Inn, Chepstow

Charlotte Moore and Her Band at The Huntsman, Shirenewton

 Fri, 17 Jul at 06:00 pm Chepstow, Monmouthshire, UK.

The Captain's Beard

 Sat, 11 Jul at 01:00 pm The Back, NP16 7DL

The Hayze Effect and Little India street food

Sat, 13 Jun at 02:00 am Monmouthshire upcycle

Chube & Dave Jones Stratospheric Live

 Wed, 01 Jul at 08:00 pm The Drill Hall Chepstow

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

 Fri, 03 Jul at 06:00 pm St Mary’s Church, Chepstow