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Past Events

Spring Afternoon Flat Racing

Today Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Switch up your Wednesday with a afternoon of leisure and some sporting fun! Join us for an afternoon of racing in Chepstow for an all-around... READ MORE>

Michelangelo - Love & Death, Exhibition on Screen film

Thu 22 May The Drill Hall Lower Church Street, Chepstow NP16 5HJ The last Exhibition on Screen film of the Season, MICHELANGELO - LOVE & DEATH, comes to the Drill Hall Chepstow on Thursday May 22 7... READ MORE>

Swing from Paris at St Mary’s Priory, Chepstow

Fri 23 May Priory Church of St Mary, Upper Church Street, Chepstow NP16 5HA An evening of Parisian-flavoured jazz and Gypsy Swing “intelligent, interesting and inventive” THE JAZZ MANN “excellent band…diverse numbers, smart... READ MORE>

Discover Clubs and Organisations in Monmouthshire

The Brutalist, award winning epic film

Fri 23 May The Drill Hall Lower Church Street, Chepstow NP16 5HJ This epic film had 10 Oscar nominations and won 3, and 9 BAFTAs taking home 4, including Best Leading Actor for Adrien Brody, and Best Cinematography... READ MORE>

Ballet to Broadway: Wheeldon Works, Royal Ballet broadcast screening

Tue 27 May The Drill Hall Lower Church Street, Chepstow NP16 5HJ The Royal Ballet’s celebration of British choreographer Christopher Wheeldon emphasises his remarkable range and highlights his verve and... READ MORE>

Friday Afternoon Racing

Fri 30 May Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Shake up your Friday with a touch of excitement and some sporting spirit! Join us for an afternoon of racing in Chepstow for an all-around fun... READ MORE>

Country & Western Racenight

Sat 7 Jun Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Saddle Up for One Night in Nashville at Chepstow Get ready for a rootin’ tootin’ country and western night like no other!... READ MORE>

Country and Western Racenight

Sat 7 Jun Chepstow Racecourse, Chepstow NP16 6EH Get ready for a rootin’ tootin’ country and western night like no other! Dust off those cowboy boots, trade your fascinator for a Stetson, and head... READ MORE>

Caerwent Car Boot Sale

Sat 14 Jun Caerwent Playing Fields Highfield NP26 5BJ join us for our ever-popular Car Boot Sale. Loads of space on the playing field. Food and drinks in our Car Boot Cafe Children's play area READ MORE>

Caerwent Car Boot Sale

Sat 14 Jun Caerwent Playing Fields Highfield NP26 5BJ Join us at our ever-popular Car Boot Sale Food and drinks at the Car Boot Cafe in the village hall. Toilets & baby-changing facilities... READ MORE>

Monday Afternoon Racing

Mon 16 Jun Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Brighten up your Monday with a touch of excitement and some sporting action! Join us at Chepstow for an all-around enjoyable atmosphere to share with... READ MORE>

Thursday Afternoon Flat Racing

Tue 17 Jun Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Switch up your Thursday with a relaxed day and some sporting action! Join us for an afternoon of racing in Chepstow for an all-around fun atmosphere... READ MORE>

Monday Summer Afternoon Racing

Mon 23 Jun Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Shake up your Monday with a touch of excitement and some sporting spirit! Join us for an afternoon of racing in Chepstow for an all-around fun... READ MORE>

Andrew Taylor - A Schooling in Murder - Book Talk

Thu 26 Jun Rossiter Books Church Street Monmouth NP25 3BX Forest of Dean based bestselling author Andrew Taylor will talk about his new historical novel, A Schooling in Murder... READ MORE>

Swing from Paris at St Nicholas Church, Grosmont

Wed 9 Jul Saint Nicholas Church, B4347, Abergavenny NP7 8LW An evening of Parisian-flavoured jazz and Gypsy Swing “intelligent, interesting and inventive” THE JAZZ MANN “excellent band…diverse numbers, smart... READ MORE>

Ladies Evening ft 80s Explosion

Fri 11 Jul Chepstow Racecourse, Chepstow NP16 6EH Ladies Day is more than an event—it’s a celebration of fun, friendship, and unforgettable moments. Perfect for birthdays, hen dos, or just because!... READ MORE>

Ladies' Evening ft. 80s Explosion

Fri 11 Jul Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH More Ladies, More Fun: Ladies Day 2025! Ladies Day races are all about feeling the adrenaline as the horses thunder down the home straight... READ MORE>

Caerwent Car Boot Sale

Sat 12 Jul Caerwent Playing Fields Highfield NP26 5BJ Join us at one of our popular Car Boot Sales. Food and drinks at the Car Boot Cafe Loads of space on the playing field... READ MORE>

Rum & Reggae Racenight

Fri 25 Jul Chepstow Racecourse, Chepstow NP16 6EH For a friendly and energetic day out, combining the best of holiday feels and sporting action. We can’t guarantee you’ll be soaking up the sun, but... READ MORE>

Rum & Raggae Carribbean Racenight

Fri 25 Jul Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Get Ready for a Caribbean Party Like No Other! For a friendly and energetic day out, combining the best of holiday feels and sporting action... READ MORE>

The Green Gathering 2025

Thu 31 Jul to Mon 4 Aug The Green Gathering Festival takes place at Piercefield Park, Chepstow, Monmouthshire NP16 6BE The UK's original off-grid, grassroots festival, The Green Gathering Festival is an eco-festival powered by sun, wind, and community... READ MORE>

Premium

Thursday Evening Racing

Thu 7 Aug Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Switch up your Thursday with a relaxed day and some sporting action! Join us for an afternoon of racing in Chepstow for an all-around fun atmosphere... READ MORE>

Caerwent Car Boot Sale

Sat 9 Aug Caerwent Village Hall & Playing Fields, Highfield, Caerwent NP26 5BJ Join us at our ever-popular Car Boot Sale. Food and drinks from the Car Boot Cafe Toilets and baby-changing facilities Children's play... READ MORE>

Thursday Afternoon Racing

Thu 14 Aug Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Shake up your Thursday with a touch of excitement and some sporting spirit! Join us for an afternoon of racing in Chepstow for an all-around fun... READ MORE>

Tuesday Evening Racing

Tue 19 Aug Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Switch up your Tuesday with a relaxed day and some sporting action! Join us for an evening of racing in Chepstow for an all-around fun atmosphere to... READ MORE>

Monday Afternoon Family Fun

Mon 25 Aug Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Fun Day Out With The Family! Looking for a fun-filled family day out Join us for our Family Fun Day and enjoy thrilling horse racing, the best... READ MORE>

Bank Holiday Family Funday

Mon 25 Aug Chepstow Racecourse, Chepstow NP16 6EH Looking for a fun-filled family day out Join us for our Family Fun Day and enjoy thrilling horse racing, the best entertainment, and a fantastic... READ MORE>

Flat Season Finale

Tue 2 Sep Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Join us for the flat season finale on Tuesday 2nd September for an afternoon of racing. READ MORE>

Mark Kermode and Jenny Nelson - Surround Sound - Book Talk

Thu 11 Sep Savoy Theatre, Church Street Monmouth NP25 5BU How can a film score make you cheer, shiver, cry or punch the air Join the UK’s favourite film critic, Mark Kermode, and radio producer Jenny... READ MORE>

Caerwent Car Boot Sale

Sat 13 Sep Caerwent Village Hall & Playing Fields, Highfield, Caerwent NP26 5BJ Join us at our ever-popular Car Boot Sale Loads of room on the playing field Food and drinks from the on-site Car Boot Cafe... READ MORE>

The Magic Of Motown

Wed 8 Oct The Riverfront, Kingsway, Newport NP20 1HG Seen by millions, The Magic of Motown is back with its 20th Anniversary Tour! It’s no surprise that this show is one of the biggest success stories... READ MORE>

Jump Season Opener

Fri 10 Oct Chepstow Racecourse, Chepstow NP16 6EH Persian War Day at Chepstow The wait is over—jump racing is back! Kick off the 2025 season in style at Chepstow Racecourse with The Unibet Jump... READ MORE>

The Unibet jump Season Opener 2025- Persian War Day

Fri 10 Oct Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH The Unibet Jump Season Opener 2025: Persian War Day at Chepstow The wait is over—jump racing is back!... READ MORE>

The Unibet Jump Season Opener 2025- Siver Trophy Day

Sat 11 Oct Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Day 2 of the Unibet Jump Season Opener 2025 The excitement continues at Chepstow Racecourse with Day 2 of the Unibet Jump Season Opener!... READ MORE>

Jump Season Opener

Sat 11 Oct Chepstow Racecourse, Chepstow NP16 6EH Silver Trophy Day at Chepstow The wait is over—jump racing is back! Kick off the 2025 season in style at Chepstow Racecourse with The Unibet Jump... READ MORE>

Jump Season Opener

Sun 12 Oct Chepstow Racecourse, Chepstow NP16 6EH Welsh Champion Hurdle Day at Chepstow The wait is over—jump racing is back! Kick off the 2025 season in style at Chepstow Racecourse with The Unibet... READ MORE>

The Unibet Jump Season Opener 2025- Welsh Champion Hurdle

Sun 12 Oct Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Day 3: The Unibet Jump Season Opener 2025 – A New Tradition Begins! The Unibet Jump Season Opener 2025 continues with Day 3, marking a brand-new... READ MORE>

Military Raceday 2025

Wed 5 Nov Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Brighten up your Friday with a friendly welcome and some sporting action! Join us in Chepstow for an all-around fun atmosphere to share with friends... READ MORE>

Autumn Afternoon Jump Racing

Fri 21 Nov Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Shake up your Friday with a touch of excitement and some sporting spirit! Join us for an afternoon of racing in Chepstow for an all-around fun... READ MORE>

Christmas Party Raceday

Sat 6 Dec Chepstow Racecourse, Chepstow NP16 6EH Christmas is around the corner – and what better way to get into the festive mood than with a day at the races at Chepstow... READ MORE>

Christmas Party Raceday 2025

Sat 6 Dec Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH The Perfect Christmas Party! Christmas is around the corner – and what better way to get into the festive mood than with a day at the races at... READ MORE>

The Coral Welsh Grand National

Sat 27 Dec Chepstow Racecourse, Chepstow NP16 6EH The 2024 Welsh Grand National at Chepstow was a resounding success, delivering an electrifying atmosphere and thrilling results... READ MORE>

The Coral Welsh Grand National 2025

Sat 27 Dec Chepstow Racecourse, St Lawrence Rd, Chepstow NP16 6EH Welcoming you back to the Welsh Grand National 2025! The 2024 Welsh Grand National at Chepstow was a resounding success, delivering an electrifying... READ MORE>

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What's On In Monmouthshire

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