A Gentleman’s Cotswolds Calendar: The Finest 50 Events of 2026

Image: Matt Higgs

There is something deeply satisfying about a year well planned. From the hum of a summer music festival drifting across open fields, to the theatre of a well-contested sporting fixture, 2026 promises a calendar rich in moments worth savouring.

This is a year for linen jackets and polished brogues, for early starts and late finishes, for weekends shaped by culture, competition and conviviality.

In this guide, we bring together the finest events of the year, from music, sport, heritage and the occasional indulgence, each chosen not for spectacle alone, but for character, craft and the pleasure of good company. Consider this your invitation to step out, lean in, and make the most of what lies ahead.

​JANUARY

GLOUCESTER v TOULON
SATURDAY 17 JANUARY • GLOUCESTER

Gloucester Rugby face a tough Champions Cup test as they host Toulon on Saturday, 17th January. With Kingsholm backing them, Gloucester will look to combine grit and flair against a star-studded Toulon side in what promises to be a thrilling contest.

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GLOUCESTER v BATH
FRIDAY 23 JANUARY • GLOUCESTER

Gloucester Rugby host Bath at Kingsholm on Friday, 23rd January, as the West Country derby comes alive with a full house under the lights. It's a game that no Gloucester fan will want to miss, and one that will sell out very quickly!

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BURNS NIGHT AT HIGHGROVE
SATURDAY 24 JANAURY

Don your best tartan and raise a toast to Scotland's national bard at our exclusive Burns Night Black Tie event at Highgrove. Classic Scottish traditions set the tone for an unforgettable evening, beginning with a beautifully curated four-course dinner. Each dish is thoughtfully prepared by Highgrove’s Orchard Room chefs, showcasing seasonal ingredients and refined flavours inspired by Scotland’s culinary heritage.

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FESTIVAL TRIALS DAY AT CHELTENHAM
SATURDAY 24 JANUARY • CHELTENHAM RACECOURSE

Excitement, anticipation and expectation is building. It is the final opportunity to see the sports protagonists go out to battle on Cheltenham Racecourse’s hallowed turf before the Cheltenham Festival. What horses will catch the eye before those four days of extraordinary in March, will we see returning champions defending their crown? Whilst anything can happen in March, Festival Trials day maybe able to give us a clearer picture.

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COCKLEBARROW RACES
SUNDAY 25 JANUARY • ALDSWORTH

Cocklebarrow Races returns this January and is always a brilliant family day out, whatever the weather. Expect sensible tweeds, practical footwear, terrier and pony racing, tug of war and lots of familiar faces in the heated picnic tent. 

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​MEN BEHAVING BADLY: THE PLAY
30 JANUARY - 7 MARCH • BARN THEATRE, CIRENCESTER

Four old friends and a wedding in the morning – what could possibly go wrong? London, 31st December, 1999. Gary’s clinging to his youth, Dorothy’s had enough, Deborah’s got a plan, and Tony’s…still Tony. When resolutions clash with revelations, the gang might just prove that the real millennium bug… is them.

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FEBRUARY

​DOM JOLY'S SPEAKEAZY
5 FEBRUARY • STEAM & WHISTLE CHELTENHAM

Dom’s Cabaret of Curiosities will have a late-night chat show vibe with guests, music & comedy. Dom wants to provide a unique, off-beat experience and the venue – The Steam and Whistle Pub and live venue opposite Cheltenham Spa station- ticks all the boxes. The idea is to have an evening that incorporates all of Joly’s interests- music, comedy, a bit of culture and a smattering of current affairs.  

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​SIX NATIONS AT DUNKERTONS
7 FEBRUARY - 14 MARCH • DUNKERTONS

With all the England games screened live, there's nowhere better to watch the Six Nations thank at Dunkertons. Their Taproom will be open and pouring all of your organic cider favourites and Guinness, while enjoying some unreal street food.

Saturday 7th February England V Wales 16:40
Saturday 14th February England V Scotland 16:40
Saturday 21st February England V Ireland 14:10
Saturday 7th March England V Italy 16:40
Saturday 14th March England V France 20:10

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​BETH ORTON
12 FEBRUARY • GLOUCESTER GUILDHALL

English singer/songwriter Beth Orton has long been regarded as possessing one of the most unique and expressive voices in music – a voice that has grown evermore rich and wise over time.

With support from special guest Sam Amidon.

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​THE SHAWSHANK REDEMPTION
10 - 14 FEBRUARY • EVERYMAN THEATRE, CHELTENHAM

Based on Stephen King’s 1982 novella, this thrilling stage production examines friendship and hope behind the claustrophobic bars of a maximum-security facility. The 1994 feature film was nominated for seven Academy Awards.​

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​GLOUCESTER V SALE SHARKS
20 FEBRUARY • KINGSHOLM

Round Nine of the Prem Rugby Cup on a Friday Night under lights at Kingsholm.

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​​THE RADIOHEAD PROJECT
28 FEBRUARY • CHELTENHAM TOWN HALL

The Radiohead Project is a stunning live tribute show that celebrates one of the greatest bands of all time – Radiohead. With Mercury Prize wins and multiple Grammy awards, their music has shaped the sound of modern alternative rock.

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​MARCH

​DOM JOLY'S SPEAKEAZY
5 MARCH • STEAM & WHISTLE CHELTENHAM

Dom’s Cabaret of Curiosities will have a late-night chat show vibe with guests, music & comedy. Dom wants to provide a unique, off-beat experience and the venue – The Steam and Whistle Pub and live venue opposite Cheltenham Spa station- ticks all the boxes. The idea is to have an evening that incorporates all of Joly’s interests- music, comedy, a bit of culture and a smattering of current affairs.  

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​THE OFFICIAL CHELTENHAM FESTIVAL PREVIEW
5 MARCH • CHELTENHAM RACECOURSE

The Official Cheltenham Festival Preview has for many years provided thousands of the racing fans with valuable information in advance of the biggest four days in jump racing.

This year’s event on Thursday 5 March 2026 will include a stellar panel, brought to you by Cheltenham's new event partner, William Hill.

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​CHELTENHAM FESTIVAL
10 - 13 MARCH • CHELTENHAM RACECOURSE

From the energy and thrill of Champion Day, to the stylish elegance of Ladies Day, every day at Cheltenham is charged with an electric atmosphere. St Patrick's Thursday brings the joy and spirit of the Emerald Isle to life while Gold Cup Day brings the festival to a close with unforgettable drama and glory.​

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​GOLD CUP GALA LUNCH
13 MARCH • THE HOLLOW BOTTOM

If you're not heading to the course on Cheltenham Gold Cup Day then the next best place is the renowned racing pub, The Hollow Bottom in Guiting Power. 

The Gold Cup Gala Lunch will include a champagne cocktail or Guinness on arrival, followed by a stunning three-course lunch throughout the afternoon while the racing is shown live on the screens.

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​THE SLATER CUP
28 MARCH • VILLA PARK, BIRMINGHAM

Ok, so this is obviously not in the Cotswolds, but it's an incredibly important fixture. The Slater Cup, named after former Gloucester and Leicester lock Ed Slater who was diagnosed with Motor Neurone Disease (MND) in July 2022, is contested between the two teams every season across each home and away Gallagher PREM fixture.

This season, Gloucester’s leg of The Slater Cup will take place at Villa Park, Birmingham, with a capacity of over 40,000. The Cherry & Whites will join Saracens and Bristol as Clubs who will host a fixture away from their home stadium, as part of the ‘Big Game’ weekend, during Round 12 in March 2026.

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​APRIL

​GIFFORDS CIRCUS
2 APRIL - 27 SEPTEMBER • VARIOUS LOCATIONS

A staple in a Cotswolds summer, Giffords Circus returns with Waterfield, a show chosen by Red and Cecil, children of founders Nell & Toti Gifford and inspired by the English countryside and the creatures that inhabit it. It will be their most ambitious show yet, with moments that make you hold your breath and acts that will have you watching through your fingers.

The show starts in Stroud, before visiting the likes of Sudeley Castle, Blenheim Palace and many other locations during the summer months.

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​SEB FONTAINE
3 APRIL • THE SUB ROOMS, STROUD

As dance music has matured, so too have the custodians that keep it vibrant. Anyone with even a cursory knowledge of the genre will know the name Seb Fontaine, the former BBC R1 selector who secured international acclaim as the movement exploded in the nineties and noughties.

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​CHELTENHAM POETRY FESTIVAL
9 - 10 APRIL • VARIOUS LOCATIONS

Cheltenham Poetry Festival offers an annual 10-day programme of exciting live literature events each spring and a year-round online programme of workshops and poetry lounges. The 2026 addition will celebrates poetry's power to enchant, entrance, and transport its readers. It will feature exciting readings, workshops and talks lined up - all of which the organisers hope, will delight and inspire you.

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​THE APRIL MEETING
15 - 16 APRIL • CHELTENHAM RACECOURSE

The April Meeting is a wonderful two-day meeting on Wednesday 15 and Thursday 16 April at the Home of Jump Racing. The Spring sunshine shining over the famous Cleeve Hill and hallowed Cheltenham turf is sure to put a spring in your step and provide a brilliant day out with high-quality racing.


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​FOR THE LOVE OF RUGBY
19 APRIL • CHELTENHAM TOWN HALL

Do you love rugby? Ben Youngs and Dan Cole do, and no men have played for England more times than them.

Newly retired, they’re taking their podcast to the stage, bringing you the best stories from across their careers. You can expect all the bits they’re too afraid to say in episodes, games, surprises and potentially a quiz. Why? For the love of the game.

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​CHELTENHAM JAZZ FESTIVAL
29 APRIL - 4 MAY • VARIOUS LOCATIONS

With the likes of David Gray, Roger Daltrey, Lulu, Tom Walker, Macy Gray, Nubya Garcia on the line-up last year, we are very excited to see who will be coming to Cheltenham for the Jazz Festival in 2026!


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MAY

​MEADOW FEST
1 - 3 MAY • CORNBURY PARK

Meadow Fest heads to Cornbury Park with a line-up that reads like a love letter to British farming and golden-era indie with Cast, The Fratellis, Sleeper, and Reef filling the early-season air with riffs, nostalgia, and the kind of anthems best sung with friends under an open sky.

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​RACE NIGHT: FEATURING ONE NIGHT IN NASHVILLE
1 MAY • CHELTENHAM RACECOURSE

The curtain comes down on the 2025/26 season with Cheltenham’s only evening fixture, and this year, they're turning up the volume! After an action-packed evening of thrilling jump racing, the party continues with One Night in Nashville – the ultimate Country music experience.

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​BADMINTON HORSE TRIALS
6 - 10 MAY • BADMINTON 

Across four days, the world’s top riders and their superb horses will be tested through the classic tri-phase challenge of dressage, cross-country and show jumping, drawing competitors and spectators from around the globe. 

Beyond elite sport there’s a vibrant atmosphere with over 500 trade stands, excellent hospitality, and plenty of shopping and social experiences set in the beautiful parkland grounds of the Duke of Beaufort’s estate

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​NICK MOHAMMED IS MR SWALLOW: SHOW PONY
20 MAY • CHELTENHAM TOWN HALL

Star of The Celebrity Traitors, Taskmaster and Ted Lasso, Nick Mohammed returns as his critically acclaimed alter-ego Mr. Swallow in the “deliriously enjoyable” (★★★★★ Guardian) Show Pony

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​BLENHEIM PALACE FOOD FESTIVAL
23 - 25 MAY • BLENHEIM PALACE

Get ready for a gastronomic extravaganza at Blenheim Palace Food Festival. Expect culinary thrills with a fantastic line-up of celebrity chefs and experts, amazing food and drink from gourmet delights to street food favourites, there will be something to tantalise every palate. 

Hear from celebrity Michelin star chefs in the festival kitchen, showcasing their passion with live demos and Q&A's and taste a range of delicious delights from the carefully selected food stalls, serving cuisine from all around the world. You can also discover a myriad of artisan kitchenware traders, craft brewers, farm shops and more.

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​WYCHWOOD FESTIVAL
29 - 31 MAY • CHELTENHAM RACECORSE

Cheltenham’s Wychwood Festival stirs up its usual magic on the racecourse, with the Kaiser Chiefs poised to deliver their trademark riot of energy. Few bands ignite a field quite like they do—big choruses, bigger smiles, and a feeling that summer has truly begun.

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​JUNE

​CHELTENHAM SCIENCE FESTIVAL
2 - 7 JUNE • VARIOUS LOCATIONS

In 2025, the Science Festival uncovered mind-blowing facts, from quantum tunnelling and the secrets of squid ink to the surprising truth that fish have legs and even what it takes to become a champion cheese chaser. We were joined by the likes of Brian Cox, Greg Foot, Maya Raichoora, Helen Czerski, Maddie Moate, Daze Aghaji, Robin Ince and more. 2026 is sure to be even bigger and better!

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​A JAMES BOND CONCERT SPECTACULAR
12 JUNE • CHELTENHAM TOWN HALL

Q The Music presents The James Bond Concert Spectacular, widely considered to be the finest performance of Bond music since the originals. Featuring all the hit title songs and some special cues from the scores, this is the most passionate, adrenaline-fueled and polished performance imaginable.

The evening will be hosted by Miss Moneypenny herself, who will guide you through the concert as compere, sharing the odd anecdote about her time in this legendary series.

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​FOREST LIVE
24 - 28 JUNE • WESTONBIRT ARBORETUM

Among the towering bark-clad giants of Westonbirt Arboretum, the beloved Forest Live series once again promises nights that feel half concert, half woodland enchantment. Richard Ashcroft will bring a voice shaped for open skies; Fatboy Slim will transform the forest floor into a glowing celebration; UB40 will drape the evening in reggae warmth; and Deacon Blue will add their blend of melody and melancholy. To hear such iconic artists beneath Westonbirt’s ancient canopy is not merely to attend a gig, it is to step into a shared moment suspended between leaves and stars.

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​BLENHEIM PALACE FESTIVAL
27 JUNE - 4 JULY • BLENHEIM PALACE

A new jewel joins the summer crown with the inaugural Blenheim Palace Festival, and it arrives with regal ambition. Neil Young, a master of songcraft whose music feels carved from wind and time, will stand before the palace’s grand façade. Alongside him, pop luminary Katy Perry brings technicolour spectacle, Pete Tong with his sun-soaked rhythms of Ibiza Classics, while Teddy Swims adds the velvet depth of a voice that seems to wrap itself around you. Global icon Alanis Morissette is the latest to be announced and will be joined by special guests Skunk Anansie for a summer evening destined to linger in the warm night air long after the final chord fades. Blenheim has long been a place for history; in 2026, it becomes a place for harmony too.​

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​JULY

​CHELTENHAM MUSIC FESTIVAL
3 - 11 JULY • VARIOUS LOCATIONS

Since 1945, Cheltenham Music Festival has proudly celebrated the love of classical music in the area. With a rich and diverse programme, the Festival brings together the world’s finest musicians alongside bold new voices shaping the future of classical music.

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​2000 TREES
8 - 11 JULY • WITHINGTON, NR CHELTENHAM

A staple of the Cotswolds summer, 2000 Trees showcases a broad mix of rock, indie and alternative acts across multiple stages, blending established artists with exciting emerging talent. The first lineup announcement for 2026 features headline appearances from bands such as Alkaline Trio alongside performances by Glassjaw, PUP, Lambrini Girls, Dinosaur Pile-Up and many others.

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​WILDERNESS FESTIVAL
30 JULY - 2 AUGUST • CORNBURY PARK

Wilderness Presented By Audi 2026 is your gateway to a weekend of boundless escapism, daring adventures, and pure joy. We celebrate individuality, creativity, and the thrill of the unexpected. Whether you're seeking moments of serenity, bursts of energy, or a chance to discover new loves; Find Your Wild.

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​CHELTENHAM 7s FESTIVAL
31 JULY - 1 AUGUST • NEWLANDS PARK, CHELTENHAM

An explosive weekend of music, fun, and unforgettable experiences. Featuring a range of competitions for Rugby, Netball, Dodgeball, and much more during the festival, with a huge line up of talented artists, bands and DJs.

The combination of sport and music is a truly unique experience which is not to be missed. You don’t have to be taking part in the sport, to be a part of this unique event. This is not just a sports festival, it is an inclusive festival. Ideal for festivalgoers, sport lovers and families. Bringing people together through music and sport.

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AUGUST

​CHELTENHAM CRICKET FESTIVAL
8 - 24 AUGUST • CHELTENHAM COLLEGE

Cheltenham Cricket Festival returns to the stunning grounds of Cheltenham College for a bumper schedule of fixtures between Saturday 8th August to Friday 24 August 2026. 

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​BIG FEASTIVAL
28 - 30 AUGUST • KINGHAM

The best music, food and family weekend of the year returns to Alex James' Farm in Kingham on August Bank Holiday. This year’s early announcements include The Streets and Bastille with the full line-up dropping soon!

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​SEPTEMBER

​SALON PRIVE
2 - 6 SEPTEMBER • BLENHEIM PALACE

Get ready for five spectacular days of automotive excellence at Blenheim Palace. Following record‑breaking attendance in 2025, the 2026 edition will take place from Wednesday 2nd September to Sunday 6th September.

The Palace lawns will once again be transformed into a glamorous garden party, where extraordinary cars are showcased alongside fine dining, champagne bars and luxury shopping - creating an unforgettable celebration of style and innovation.

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​CORNBURY HOUSE HORSE TRIALS
9 - 13 SEPTEMBER • CORNBURY PARK

An eventing experience set amongst the beautiful woodland of the Cotswolds’ most prestigious estate. Cornbury House Horse Trials is the ideal setting to see some of the the finest young horses and riders in the country competing in dressage, cross country and show jumping across five days in September.

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​BLENHEIM PALACE INTERNATIONAL HORSE TRIALS
17 - 20 SEPTEMBER • BLENHEIM PALACE

Get ready for an unforgettable experience this year at Blenheim Palace! Experience four days of exhilarating eventing, including Dressage, Cross Country, and Showjumping, set against the stunning backdrop of Blenheim Palace – one of Britain’s most beautiful and historic venues.

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OCTOBER

​CHELTENHAM LITERATURE FESTIVAL
9 - 18 OCTOBER • VARIOUS LOCATIONS

Cheltenham Literature Festival is the world’s longest-running literature Festival, leading the way in celebrating the written and spoken word. Each year we present the best new voices in fiction and poetry alongside literary greats, high-profile speakers and inspiring thinkers.

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​THE SHOWCASE
TBC • CHELTENHAM RACECOURSE

The first meeting of the season at The Home of Jump Racing. Two days of great racing to get your heart pumping for the season ahead.

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​CHARIOTS OF FIRE
20 -24 OCTOBER • EVERYMAN THEATRE, CHELTENHAM

Two men. One Olympic dream. One running for faith. The other to prove his worth. Based on the multi-Oscar and BAFTA -winning film, Chariots of Fire is inspired by the extraordinary true story of Eric Liddell and Harold Abrahams as they strive for glory at the 1924 Paris Olympics.

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​PHIL WANG: UH OH
23 OCTOBER • CHELTENHAM TOWN HALL

UH OH. Phil Wang’s back with a new stand-up show, and he’s older than ever before. He’s got a moustache now. It bristles with wisdom. His eyes shine with good humour. His shoulders groan under the weight of being the only cool millennial left. Everyone’s an idiot but him. Nice is out. Right is in. The vibe shift is real. Old Wang’s riding it.

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​FILM CHELT
30 OCTOBER - 8 NOVEMBER • VARIOUS LOCATIONS

Established in 2025, FilmChelt is an independent film festival, run by a not for profit charity bringing an exciting programme of films and events to the heart of Cheltenham.

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NOVEMBER

​PROFESSOR BRIAN COX: WORLD TOUR
4 NOVEMBER • THE CENTAUR, CHELTENHAM RACECOURSE

After performing his smash-hit show ‘Horizons’ to nearly half a million people across the world, Professor Brian Cox is back with his new tour world tour Emergence.

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​THE NOVEMBER MEETING
TBC • CHELTENHAM RACECOURSE

The weekend starts with Countryside Day, celebrating rural life and tradition alongside top-class sport, before diving into Super Saturday, where the energy is electric, racing reaches its peak against the stunning Cotswold hills, and the post-racing celebrations raise the roof. Finally, enjoy the community spirit of Carnival Sunday, where there's something for everyone to enjoy.  

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DECEMBER

​THE CHRISTMAS MEETING
TBC • CHELTENHAM RACECOURSE

Festivities start at Cheltenham for The Christmas Meeting. Don your finest Christmas jumper and enjoy two days of superb racing.

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