May is a month we hope is filled with sunshine and fun! Given the Jazz Festival and Hunter Chase Rading both take place on a Bank Holiday weekend, how can it not be? Here’s our top picks of what’s on to enjoy in Cheltenham throughout the month...

Cheltenham Jazz Festival 2018

Date: 2nd – 7th May 2018

Location: Montpellier Gardens, Cheltenham

This year’s Jazz Festival will be kicking off at the beginning of this month for six days. Located in the beautiful Montpellier Gardens, it’s the perfect event for all the family with performances, workshops, sing-alongs, and the Big Top Stage, all within the tented festival village. American singer Randy Crawford will be opening the festival on the 2nd of May with an exciting performance! Even better, more than 60% of the events are totally free, so take a look at what you can enjoy in our Beginner's Guide to the Festival

Book tickets...

Hunter Chase Evening

Date: 4th May 2018

Location: Cheltenham Racecourse, Evesham Road, Prestbury, Cheltenham, Gloucestershire, GL50 4SH

Start your bank-holiday weekend with a fun-filled evening of racing! Amateur jockeys get together at racing’s ‘Theatre of Dreams’ to celebrate the season finale of Cheltenham racing! The evening will culminate with well-known DJs Jo Whiley and Huw Stephens hosting a live set after the racing for the ever-popular after party! 

Get your tickets here...

Suffolks Sunday Market

Date: 6th May 2018

Location: The Suffolks, Suffolk Road, Cheltenham, GL50 2AF

A fantastic day with more than 20 pop-up stalls, buskers and food vendors, combining to create a hustling, bustling vibe in the town. Definitely worth a stop!

Full event details...

PDSA PetLife Festival 2018

Date: 6th May 2018

Location: Cheltenham Racecourse, Evesham Road, Prestbury, Cheltenham, Gloucestershire, GL50 4SH

Pet wellbeing charity PDSA is bringing their PetLife festival to Cheltenham Racecourse this year! The festival will be full of family-fun and music from huge artists such as the Kaiser Chiefs, Jessie J and The Vamps. The day will celebrate the pets we love and will include dog-tastic events such as dog agility displays, funfairs, military bands and more! Be sure to register your dog as places are limited to 2000 dogs!

Full event details...

Tea & Cakes with an historic twist

Date: 12th May 2018 - 11am to 3pm

Location: The Holst Museum, 4 Clarence Road, Pittville, Cheltenham, Gloucestershire, GL52 2AY

Step back in time with a trip to the Holst Museum, where for one day only, visitors will enjoy seasonal Victorian Treats baked fresh in the historic basement kitchen...

Full event details...

Curry & Colonels

Date: 12th May 2018

It might seem like a strange combination, but did you know Cheltenham has Indian connections and Raj history. This newly launched tour of Cheltenham is led by Skillicorne, culminating in a delicious meal at East India Cafe! Bargain!

Full details...

Cheltenham Cocktail Week 2018

Date: 14th - 19th May 2018

Location: Various Venues in Cheltenham

Cheltenham’s second Cocktail Week kicks off on the 14th May and is set to offer an exciting line-up of events across the town's fantastic pubs, bars, clubs and restaurants! Eight different venues will be bringing a range of unique events, including the opening party with Absolut Vodka and a Champagne brunch with Perrier Jouet Champagne! Oh and don't forget the exclusive trio of cocktails mixed just for this week!

Find out more about the full line-up of events here.

'A Chronicle of War Work' Exhibition

Date: 14th - 25th May

Location: Parabola Arts Centre, Parabola Road, Cheltenham, Gloucestershire, GL50 3AA

As part of Cheltenham's WW1 commemorative events, Cheltenham Ladie's College has put together this exhibition, chronicling the work done by its pupils in the first world war...

Full event details...

Dire Straits Experience

Date: 19th May

Location: Cheltenham Racecourse, Evesham Road, Prestbury, CHELTENHAM, Glos, GL50 4SH

Returning to where it all began for the singer, former Dire Straits touring member Chris White will be bringing this phenomenal concert experience to the Town...

Full event details...

Summer of Steps

Date: 26th May

Location: LCI Rail Stadium, Whaddon Rd, Cheltenham, Gloucestershire, GL52 5NA

If you were one of the many thousands of fans of Steps, then you'll NEED to attend their reunion tour, coming to Cheltenham at the end of the month. Don't forget, we have a competition to win tickets over on our Facebook page. What are you waiting for?

Full event details...

Chase a cheese anyone?

Date: 26th May

Location: Coopers Hill, Gloucester, Gloucestershire, GL3 4SB

It might seem like madness, but one of the local Cheltenham traditions is to chase a DoubleGloucester Cheese down a VERY big hill! Yes, really! You have to see it to believe it, and lucky for you, it's on at the end of May!

Full event details...

Theatre and Comedy

If you fancy a tip to the theatre there is plenty on offer at The Everyman Theatre. Here’s just a selection of the great shows on this month:

  • 29th May- 3rd June (Everyman Theatre):  Hairspray the Musical – feel-good musical comedy show featuring hit songs such as Welcome to the 60s, You Can’t Stop The Beat and more! Book here...
  • 8th – 12th May (Everyman Theatre): Great Expectations – the classic Dickens play comes to Cheltenham’s Everyman with a brand-new and exciting stage adaptation. Book here...

Plan ahead for June...

May may be jam-packed, but that's only the beginning of our event season! Don't forget to plan ahead and grab your tickets for...


Wychwood Music Festival 2018
Wychwood Music Festival 2018

A family-friendly festival of music, comedy cinema, creative workshops and lively ethical debate in the attractive setting of Cheltenham Racecourse overlooked by the Cotswold Hills...

Cheltenham Food and Drink Festival
Cheltenham Food and Drink Festival

The Cheltenham Food & Drink Festival is a gastronomic delight, with over 150 exhibitors, the scope of local & regional products on show ensures there is something for everyone...



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