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Cheltenham 2020 Calendar Highlights

Cheltenham or ‘Cheltenham Spa - Festival town of England’, is not only the centre for the Cotswolds, it’s home to some of the best recognised, and most prestigious festivals around the world.

Why is Cheltenham the ‘Festival town of England’?

It hosts more major festivals than any other town in England.

‘Not to be missed’ festivals and events to look forward to in Cheltenham 2020

January & February 2020

The pantomime season draws to an end and a new season begins at The Everyman Theatre. January kicks off a great season with "The Croft" followed by "Six" the smash hit musical from the 'wives' of Henry VIII. February sees a new Everyman Theatre production of 'The Missing Company of Sherlock Holmes' starring Tweedy.

March 2020

Probably the most famous sporting festival in England occurs in mid March. With daffodils in full bloom and race-goers swarming the streets of Cheltenham, the Cheltenham National Hunt Festival brings the Regency town to life! Spread over four days from 10  - 13 March it finishes with the 'blue-riband' event, the ‘Cheltenham Gold Cup’. The atmosphere is electric and the buzz of excitement can be felt miles away!

Sandford Parks Lido opens on 30 March (tbc). Their 50m outdoor pool and children's pool is a great way to relax and enjoy the Spring sun. Look at for many events at the Lido too this year!

April 2020

Look out for Easter events in and around the town including a family Easter trail at Primrose Vale.  


May 2020

May sees the start of the Cheltenham Jazz Festival (5 - 10 May) – one of Europe’s leading jazz festivals. It’s great for all jazz lovers, with funk, blues, latin and soul.

Cheltenham also hosts the Cheltenham Competitive Festival. It's a celebration of dance, music, speech and drama attended by thousands of competitors of all ages showcasing some of the talent that Gloucestershire has to offer.

June 2020

From the 2 - 7 June 2020, Cheltenham hosts the UK’s premier science festival, bursting with talks, shows, debates, workshops and hands-on activities. Adults and children love it as it opens the mind to a kaleidoscope of exploration and fun.

Gloucestershire County Cricket Club battle it out with other county teams during the annual Cheltenham Cricket Festival in the grounds of Cheltenham College from 29 June - 9 July. It’s a small, friendly and picturesque ground and this helps create some wonderful and exciting cricket.

From 29 - 31 May at the Cheltenham Racecourse is a weekend of musical indulgence courtesy of the Wychwood Music Festival.

July 2020

The Cheltenham Music Festival from 3 - 12 July - with national and international classical musicians.

September 2020

September sees a break from festivals, but the start of the autumn season will undoubtedly bring some great plays to the Everyman Theatre, while comedy can be enjoyed at the Cheltenham Town Hall courtesy of Howlers Comedy Club.

Watch out for the Cheltenham Triathlon - helping raise funds for LINC (Leukaemia Intensive Chemotherapy) and Sandford Lido Limited.

October 2020

The autumn season continues at The Everyman Theatre and more endurance can be seen in the ultra-tough Devil's Aquathlon at Sandford Parks Lido.

Book your tickets early to see some famous and familiar faces appearing at the Cheltenham Literature Festival from 2 - 11 October.

November 2020

It’s another bumper packed few days of horse racing at The November Meeting from 13 - 15 November with top national and international horses taking on past and current champions in what is classed as one of the best early season meetings.

Look out for Tweedy again when he appears in the pantomime Jack and the Benstalk at The Everyman Theatre which begins at the end of the month.

December 2020

Cheltenham is famous for its shopping and with it’s tree-lined Promenade, cosmopolitan Montpellier, Regent Arcade Shopping Centre and The Brewery leisure complex  ‘Christmas Shopping in Cheltenham’ is a pleasure. Watch out for the continental markets, street entertainment and the beautiful Christmas lights and illuminations, which decorate the town centre and charming parks and gardens.


Explore Gloucestershire are continually updating our events listings, so follow the link below to find a comprehensive list of events happening in and around Cheltenham.

Forthcoming festivals and events in Cheltenham in 2020...

Please check with the contact telephone numbers or websites before planning your visit. Sometimes events can be cancelled for various reasons and we wish you to enjoy your day out.

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