Get ready to fill your calendars!  May is an absolute whopper of a month with over 100 events in Cheltenham.  There is something going on for ALL ages and interests.  We’ve rounded up some of the best events below.  Make sure you check out our What’s On section of the website for smaller, community led events. (Updated 15th May). 

Cheltenham Cocktail Week 2019

10th - 18th May

For the third year running, Cheltenham Cocktail Week returns offering the opportunity to see behind the bar at your favourite venues, experience new and adapted exclusive drinks, live bands and food & drink pairings designed especially for a week of celebrating the art of mixology. Check here for our full list of events and participating venues.

The Suffolks Sunday Market

The Suffolks

26th May

The Suffolks run several Sunday Markets annually including buskers, street food and over 80 stalls.  More info here.

Giffords Circus, Sudeley Castle

16th May - 28th May 

Giffords Circus has returned to Sudeley Castle to entertain with miracles, song, symphony and enchantment. You can expect musicians, horses, clowns and tumblers performing a 70's themed show.  Book your tickets via the Everyman Theatre

Arts & Crafts Market

18th May


The monthly Arts & Crafts market brings together local producers, crafters and artisans to create a market full of unique gifts, homeware and handmade goods. More details here.

Cheltenham Festival of Cycling 2019

Sunday May 19th 

Pittville Park

The festival will host a range of fun family friendly activities celebrating everything cycling from 10am to 5pm. More info here.

Craig David in concert at Cheltenham Town FC

Friday May 24th 

In the wake of massive success of his 2018 tour, Cheltenham will form part of a limited number of concerts across the UK in the summer of 2019, bringing Craigs warmth and a phenomenal live show. More details here.

Cheltenham International Film Festival

Bank Holiday Monday 27th May – 1st June

A parade of celebrated filmmakers, led by Mike Leigh, are coming to town. Throughout the six days of the Festival, the organisers will screen, in competition, the best of independent cinema from around the world. For more information about the 45 events taking place click here.

Wychwood Festival

Cheltenham Racecourse

Friday May 31st – 2nd June

The UK's favourite family festival takes place in the grounds of Cheltenham Racecourse.  Over 100 acts perform across four stages, plus music, dance and arts workshops, a circus school and a programme of talks, debates and comedy for all ages. More info here.

Cheltenham Farmers Market

Every other Friday

The Promenade

Stalls line the street selling a range of produce including various meats and charcuterie, fruit and vegetables, desserts, preserves and pickles, cakes, bread, cheese and plants.  More info here.

Cheltenham Fine Food and Drink Market

First Saturday of every month between March & December.

The Promenade outside Cavendish House / House of Fraser.

Supporting artisans in the rural economy, Cheltenham Fine Food & Drink Market brings together local producers and purveyors of local delicacies and handmade delights. Whether you're a fudge fanatic or a pie pursuer, there's something on offer.  More info here.

Cotswolds Festival of Steam

Gloucestershire Warwickshire Steam Railway

25 May to 27 May 2019

A chance to experience travelling on lots of different locomotives all on the same day. More info here.

Prescott Hill Climb – La Vie en Bleu incorporating La Vita Rossa

25 May - 26 May

The spectacular two-day event is a firm favourite on the motoring calendar and celebrates all things French & Italian. Click here for more info.

The Suffolks May Fair

26th May

Free event for the whole family.  The Suffolks Street Fair returns to the Cheltenham shopping quarter with stalls, music, a childrens area and street entertainment. More info here.  

Cheltenham Food and Drink Festival

14th – 16th June

Montpellier Gardens

One of the UK's top foodie events. Feast on tasty treats galore during a jam-packed menu offering everything from chef demonstrations and wine tastings, to live music and street theatre. More details here.

Flying Trapeze Classes

Pittville Park

Weekends until the 20th October

Flying Trapeze classes for any level including absolute beginners. Learn to fly on a full size flying trapeze rig over a nice soft net. More details




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