All Upcoming events

• Sat, 10 Jan, 2026 - 09:00 AM

  Pony Club Team Friendly & Winter Series (2)

  David Broome Event Centre

  180+ Interested
• Sat, 18 Jul, 2026 - 10:00 AM

  Soul & Sage at the Racecourse

  Chepstow Racecourse

  187+ Interested
• Sat, 14 Feb, 2026 - 07:00 PM

  Llanthony Secunda Manor Ghost Hunt

  Llanthony Secunda Manor

  24+ Interested
• Fri, 03 Jul, 2026 - 07:00 PM

  Borderlands Country Weekender

  Chepstow Rugby Club

  50+ Interested
• Sat, 17 Jan, 2026 - 06:00 PM

  Wassail 2026

  NP26 3GD

  Free
• Sat, 17 Jan, 2026 - 07:00 PM

  Llanthony Secunda Manor Ghost Hunt Sleepover - £79 P/P

  Llanthony Secunda Manor

  6+ Interested
• Sat, 28 Feb, 2026 - 09:00 AM

  2026 Under 15s Knights Pairs & Winter Series (3)

  David Broome Event Centre

  114+ Interested
• Sat, 10 Jan, 2026 - 09:45 AM

  Chepstow, Monmouthshire, Iris Photography Pop-Up

  Tidenham Memorial Hall
• Sat, 31 Jan, 2026 - 10:00 AM

  Stained glass intensive weekend – 31st Jan & 1st Feb

  Chepstow Art Space, Upper Nelson Street, NP16 5PG
• Wed, 14 Jan, 2026 - 07:30 PM

  Comedy Night at Colin's

  25a St Mary’s Street, NP16 5EU Chepstow, United Kingdom

  22+ Interested
• Wed, 21 Jan, 2026 - 06:00 PM

  Kundalini Activation Process- Group Session BATH

  Stone Rock Lodge
• Fri, 16 Jan, 2026 - 07:00 PM

  SOLD OUT! Llanthony Secunda Manor Ghost Hunt Sleepover - £79 P/P

  Llanthony Secunda Manor

  8+ Interested
• Sun, 18 Jan, 2026 - 11:00 AM

  Chepstow Art Space Jam Session-18th January

  Chepstow Art Space, Upper Nelson Street, NP16 5PG

  28+ Interested
• Fri, 27 Feb, 2026 - 08:30 PM

  MALAGO CANYON- 27th February- FREE EVENT

  Chepstow Art Space, Upper Nelson Street, NP16 5PG

  4+ Interested
• Sat, 24 Jan, 2026 - 12:00 PM

  Chepstow Wassail and Mari Lwyd. Hosted by Widders Border Morris

  Chepstow Town Centre

  800+ Interested
• Sat, 28 Feb, 2026 - 10:00 AM

  The Babywear Drop-In: Help Shape Our Next Organic Collection!

  Caldicot

  Free
• Thu, 08 Jan, 2026 - 07:00 PM

  Line and watercolour illustration course – starting 8th January 2026 (4weeks)

  Chepstow Art Space, Upper Nelson Street, NP16 5PG

  9+ Interested
• Mon, 19 Jan, 2026 - 07:30 PM

  Chepstow’s Roman Crossing

  Tidenham Memorial Hall, Coleford Road, Tutshill, Chepstow

  6+ Interested
• Sat, 31 Jan, 2026 - 11:00 AM

  January Craft & Produce Market

  Caerwent Village Hall & Playing Fields

  21+ Interested
• Sat, 28 Nov, 2026 - 08:00 PM

  Caldicot Castle

  Caldicot Castle

  7+ Interested
• Sat, 25 Apr, 2026 - 08:00 PM

  Caldicot Castle Monmouthshire Ghost Hunt

  Caldicot Castle

  36+ Interested
• Thu, 08 Jan, 2026 - 05:00 PM

  Monmouthshire Antenatal Course

  West End Flying Start

  Free
• Sat, 10 Jan, 2026 - 10:30 AM

  Lego Workshop

  Caldicot Community Hub

  Free
• Sat, 10 Jan, 2026 - 10:00 AM

  January Chepstow Repair Cafe

  Monmouthshire Upcycle, Station Yard Industrial Estate,, Chepstow

  6+ Interested
• Sat, 07 Feb, 2026 - 07:00 PM

  THE LABOURERS – 7th February

  Chepstow Art Space, Upper Nelson Street, NP16 5PG

  8+ Interested
• Sun, 01 Feb, 2026 - 02:00 PM

  Rock It! Rog'it

  Severn Tunnel Non Political Club

  17+ Interested
• Tue, 06 Jan, 2026 - 11:00 AM

  Gentlemen community club

  Cherry Tree Care Home
• Thu, 08 Jan, 2026 - 07:30 PM

  Off-Road Night Race - Chepstow Racecourse and Piercefield Park

  Chepstow Race Course

  128+ Interested
• Sun, 03 May, 2026 - 10:00 AM

  South Wales Car Festival 2026

  Chepstow Racecourse

  488+ Interested
• Fri, 06 Nov, 2026 - 05:30 PM

  Secunda manor ghost hunt

  Llanthony Secunda Manor

  23+ Interested
• Sat, 17 Jan, 2026 - 10:00 AM

  Tree planting on the Rec

  Tidenham War Memorial and Recreation Ground Trust

  7+ Interested
• Thu, 12 Feb, 2026 - 10:00 AM

  Start A Side Hustle

  Caldicot

  Free
• Sat, 17 Jan, 2026 - 10:00 AM

  Book Fair

  43 Newport Road, NP26 4BQ Caldicot, United Kingdom

  51+ Interested
• Sun, 08 Mar, 2026 - 11:00 AM

  St Tewdrics House Wedding Fair

  St Tewdrics House
• Sat, 17 Jan, 2026 - 10:00 AM

  Chepstow Racecourse, Wales, NP16 6BE

  Chepstow Racecourse

  17+ Interested
• Mon, 19 Jan, 2026 - 02:00 PM

  MEDIEVAL MYSTERIES, art history & appreciation course

  The Drill Hall Chepstow

  4+ Interested
• Mon, 12 Jan, 2026 - 10:00 AM

  Bore Coffi

  TogetherWORKS, Woodstock Way, Caldicot
• Sat, 17 Jan, 2026 - 10:00 AM

  Apple Pruning in Bulwalk

  Cofira Coffee Shop

  10+ Interested
• Sun, 19 Jul, 2026 - 09:00 AM

  Wye Valley Tunnel Run 19th July 2026

  Wyedean School

  184+ Interested
• Sat, 31 Jan, 2026 - 09:00 PM

  The Modul8tors

  The Three Tuns

  7+ Interested
• Thu, 22 Jan, 2026 - 07:00 PM

  HAMLET, National Theatre new production filmed live, screening

  The Drill Hall Chepstow

  8+ Interested
• Fri, 16 Jan, 2026 - 07:00 PM

  A Hans Zimmer Candlelight Experience In Chepstow🕯️Friday 16th January

  St Mary’s Church, Chepstow
• Sat, 28 Feb, 2026 - 05:00 PM

  Dancing Thru The Decades 🎶

  Mounton Brook Lodge - Chepstow

  24+ Interested
• Sun, 15 Feb, 2026 - 04:00 PM

  Family Worship

  St James The Great Devauden
• Sat, 24 Jan, 2026 - 10:00 AM

  Winter pruning The Dell Orchard

  Chepstow Castle

  6+ Interested