Upcoming Caldicot Events

Check out what's happening 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

Dr John Cooper Clarke with special guest Mike Garry

 Thu, 30 Apr at 07:30 pm Blake Theatre Monmouth

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

Jungle Syndicate Weekender 2026

 Fri, 22 May at 12:00 pm Piercefield Park

Phil Campbell & The Bastard Sons - Chepstow Castle

 Sat, 22 Aug at 05:00 pm Bridge St, Chepstow NP16 5EY

MABON

 Fri, 25 Sep at 06:00 pm Caldicot Castle, Church Rd, Caldicot NP26 4HU

As December Falls, Lake Malice, Tigress in

 Sat, 15 Aug at 07:00 pm Chepstow Castle

Wye Valley Tunnel Run 19th July 2026

 Sun, 19 Jul at 09:00 am Wyedean School

ABCM + SMALL FAKERS + 2RUDE // CHEPSTOW CASTLE

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

Benny Page in Chepstow

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

Scarlet Rebels & Friends

 Fri, 21 Aug at 07:00 pm Bridge St, Chepstow NP16 5EY

Medieval Music Day - Chepstow Castle

 Sat, 20 Jun at 10:00 am Chepstow Castle

Soul & Sage at the Racecourse

 Sat, 18 Jul at 10:00 am Chepstow Racecourse

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

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

 Sun, 26 Apr at 10:00 am Chepstow Racecourse

Scarlet Rebels headline Chepstow Castle

 Fri, 21 Aug at 12:00 pm Chepstow Castle

Caldicot Castle Monmouthshire Ghost Hunt

Sat, 25 Apr at 08:00 pm Caldicot Castle

Dirty Dancing v´s Grease

 Sat, 11 Jul at 07:00 pm Mounton Brook Lodge - Chepstow

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

Chepstow Summer Vegan Market

 Sun, 30 Aug at 10:00 am High Street, Chepstow, NP16 5, United Kingdom

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

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

Caldicot Castle Monmouthshire Spooky Season Ghost Hunt

Sat, 03 Oct at 08:00 pm Caldicot Castle & Country Park

Becki Biggins Live in Concert - Chepstow

 Sat, 02 May at 07:30 pm The Drill Hall Chepstow

An Evening with Maggie Aderin

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

Gwyl Hwyl Cas-Gwent 2026

 Sat, 04 Jul at 10:00 am High Street, Chepstow, NP16 5, United Kingdom

Chepstow MBS Show 2026

 Sat, 17 Oct at 10:00 am Chepstow Racecourse

HAMNET

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

St Tewdrics House Evening Wedding Fair

 Tue, 23 Jun at 06:30 pm St Tewdrics House

Open Farm & Dog Show

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

Borderlands Country Weekender

 Fri, 03 Jul at 07:00 pm Chepstow Rugby Club

Chepstow castle fun day

 Sat, 16 May at 11:00 am Chepstow Castle

Romeo and Juliet 🥀

 Thu, 28 May at 07:30 pm The Drill Hall Chepstow

0-5 years Baby and Children’s Clothes Sale

 Sun, 26 Apr at 09:00 am Drill hall, Lower Church Street, Chepstow

David Hanratty & His Band and Special Guest

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

Monthly Indoor Table Top Sale

 Sat, 25 Apr at 10:00 am 43 Newport Road, NP26 4BQ Caldicot, United Kingdom

BASS ODYSSEY DAY FEST

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

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

Magor May Fayre 2026

 Mon, 04 May at 01:00 pm Magor

MGAGB Spring Championships 2026

 Sat, 25 Apr at 08:00 am David Brooms(Cricklands)

CONCERT IN St. MARY@S PRIORY IN CHEPSTOW TO AID SARA

Sat, 25 Apr at 06:30 pm Upper Church Road, Chepstow

Epoxy resin wave olive wood heart – Starting 14th May 2026 (2 weeks)

 Thu, 14 May at 06:00 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

THE MAGIC FLUTE, broadcast screening from the Royal Opera

 Sun, 26 Apr at 02:00 pm The Drill Hall Chepstow

Recreational Ride - Spring is here! OPEN TO EVERYONE

 Wed, 22 Apr at 06:30 pm The Millers Arms

Bryan Chapman Memorial 600km - CYCLE EVENT - Audax UK

 Sat, 16 May at 06:00 am Bulwark Community Centre, Chepstow

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

 Tue, 16 Jun at 07:00 pm Pontio Lounge

Evening of Mediumship with Nikki Kitt - Chepstow

 Wed, 10 Jun at 07:30 pm The Drill Hall Chepstow

Monmouthshire Antenatal Course

 Thu, 17 Sep at 05:00 pm West End Flying Start Family Centre Free

Make a Hidden Message Ring - Silversmithing Workshop

 Wed, 27 May at 06:00 pm 16 Moor Street, Chepstow, NP16 5DB, United Kingdom

Els Errorets- Free live music at Chepstow Art Space

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

Ophelias Beard- captivating music and artful vibes

 Fri, 03 Jul 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

THE BLOOMSBURY GROUP illustrated talk about the groundbreaking artists

 Tue, 28 Apr at 07:30 pm The Drill Hall Chepstow

Summer Fayre 2026

Sat, 20 Jun at 12:00 pm St Mary’s RC Primary School

Line dance Flash Mob

 Sat, 02 May at 11:00 am Caldicot Town Team

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

DAMAGED GOODS & BUSTERS BURGERS

 Sat, 02 May at 04:00 pm Mathern, Monmouthshire, United Kingdom

Classic rock n pop

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

Bethany Chadd // Saturday Afternoon Music // Free Entry // The Boat Inn

 Sat, 09 May at 03:30 pm The Boat Inn, Chepstow

Experience The Beatles at Chepstow Drill Hall

 Sat, 05 Sep at 12:00 am The Drill Hall Chepstow

Ford Fanatics South Wales @ Fords at the castle

Sun, 26 Jul at 09:00 am Caldicot Castle & Country Park

Chube & Dave Jones Stratospheric Live

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

Indian Block Printing Workshop

 Sat, 20 Jun at 10:30 am St Arvans Memorial Hall, Nr Chepstow NP16 6EJ

👰🏼Wedding Day parkrun🤵🏻

 Sat, 23 May at 08:30 am Severn Bridge Parkrun

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

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

Chepstow Bowls Club Open Day & Welcome Evening

 Sun, 17 May at 11:00 am Chepstow Bowling Club, Mathern Road, , NP16 5JT Chepstow, United Kingdom

The Modul8tors

 Sat, 26 Sep at 09:00 pm The Two Brewers

Pauline Porter Populaire

 Fri, 15 May at 07:00 am Bulwark Community Centre, Chepstow

Pet Blessing

Sun, 03 May at 11:30 am Penterry Church, Penterry Lane, NP16 6HQ ·

Ryan Haynes // Saturday Afternoon Music // Free Entry // The Boat Inn

 Sat, 16 May at 03:30 pm The Boat Inn, Chepstow

Kundalini Activation Process- Group Session Chepstow

 Wed, 22 Apr Stone Rock Lodge

Line and watercolour course – starting 4th June 2026 (4weeks)

 Thu, 04 Jun at 07:00 pm Chepstow Art Space, Upper Nelson Street, NP16 5PG

Girls, Let’s Go! Beauty and Relaxation Event

 Sat, 02 May at 01:00 pm 2Thomas St , NP16 5DH Chepstow, United Kingdom

Wye Knot Speakers Toastmasters Public Speakers Club Meeting

 Wed, 22 Apr at 07:15 pm The Board School, Bridge Street, NP16 5EZ Chepstow, United Kingdom

Crossing your threshold into Love with the Llwyna Herd.

Sat, 30 May at 09:00 am Llwyna Farm, Monmouthshire

Lego Workshop

 Sat, 25 Apr at 10:30 am Caldicot Community Hub Free

CMVC Taster Evening

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

Mothers Ruin

 Mon, 18 May at 07:30 pm Tidenham Memorial Hall, Coleford Road, Tutshill, Chepstow

Shiatsu Workshop

Mon, 15 Jun at 07:00 pm Tidenham Memorial Hall, Coleford Road, Tutshill, Chepstow

Jomalig Island • Quezon Province | 3D2N

 Fri, 22 May at 11:00 am Online event

999 Emergency Services Event 2026

 Sun, 23 Aug at 10:00 am Caldicot Castle & Country Park