Entertainment events in Caldicot

Check out happening entertainment events all around Caldicot, WA

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

Monster Truck Motorfest Chepstow

 Sat, 04 Jul at 10:00 am Chepstow Racecourse

South Wales Car Festival 2026

 Sun, 03 May at 10:00 am Chepstow Racecourse

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

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

Benny Page in Chepstow

 Sat, 02 May at 05:00 pm The Lion Lounge

ABCM + SMALL FAKERS + 2RUDE // CHEPSTOW CASTLE

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

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

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

Caldicot Street Food Festival Series 2026

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

The ELVIS Show @ The Drill Hall, Chepstow

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

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

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

⭐MEGA⭐ Musical Bingo at The Two Brewers (Chepstow) - Friday 24th April 7pm

 Fri, 24 Apr at 07:00 pm The Two Brewers

An Evening with Maggie Aderin

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

HAMNET

 Fri, 24 Apr at 07:30 pm The Drill Hall Chepstow

Open Farm & Dog Show

Sun, 17 May at 10:30 am Lower House Farm , NP16 6LX Llanvair Discoed, United Kingdom

David Hanratty & His Band and Special Guest

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

OPA ROSA-Bristol based energetic balkan and klezmer sounds from Eastern Europe!

 Fri, 01 May at 08:30 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

BASS ODYSSEY DAY FEST

Sat, 02 May at 02:00 pm The Lion - Chepstow

Magor May Fayre 2026

 Mon, 04 May at 01:00 pm Magor

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

 Tue, 16 Jun at 07:00 pm Pontio Lounge

Els Errorets- Free live music at Chepstow Art Space

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

One-Two Live @ The Five Alls, Chepstow

 Sat, 16 May at 08:30 pm The Five Alls

Groove Jacks LIVE- Hive Mind Mead & Brew Co

 Sat, 25 Apr at 09:00 pm Hive Mind Mead & Brew Co

The Captain's Beard

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

Classic rock n pop

 Sat, 25 Apr at 09:00 pm The Cross Inn Caldicot

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

CMVC Taster Evening

 Mon, 27 Apr at 07:00 pm Dell Primary School