What a year we have planned for you in Cheltenham!

Below is a summary of 40+ major races, events and festivals we are proud to be hosting in 2020 here in Regency Cheltenham, The Festival Town including Cheltenham Cricket Festival which is celebrating its 150th anniversary this year and Cheltenham Literature Festival which celebrated its 70th year in 2019.

Make sure you add these dates to your calendar so you don’t miss out!  Many of these are annual events, others are a one off.  We have clearly highlighted these so you can make plans for future visits to Cheltenham.

In 2019 over 1,500 events were listed on the Visit Cheltenham website so we recommend you check our what’s on and things to do pages regularly for weekend and short break inspiration.

Visitors tell us time and time again that one day is not enough to experience our spa town, the most complete Regency town in the UK.  Why not plan to attend an event listed below and then extend your stay for a few nights?  Check out our recommended Cheltenham hotels for every type of accommodation you could possibly wish for from spa hotels to self-catering apartments and guest houses.

With many award winning restaurants and bars Cheltenham is truly a foodie paradise. Our eating out recommendations are guaranteed to convince you to stick around for a few days to indulge. (Just make sure you pack some clothes with an adjustable waistband!)

Without further ado here are the 40+ major races, events and festivals taking place in Cheltenham in 2020…


January 2020

New Year’s Day Races 

Location: Cheltenham Racecourse, Prestbury, Cheltenham, GL50 4SH

Date: 1 January. Annual event

Festival Trials Day

Location: Cheltenham Racecourse

Date: 25 January. Annual event

Cheltenham Boutique Sale

Location: Cheltenham Ladies College, Princess Hall, Cheltenham, GL50 3EP

Date: 26 January. Annual event


February 2020

Light Up Cheltenham

Location: 30+ buildings lit up across town.  Observation wheel in Imperial Gardens

Dates: 1 to 23 February. Annual event

Coral World Grand Prix Snooker

Location: Cheltenham Racecourse

Dates: 3 – 9 February. Annual event (2nd year)

The Cheltenham Masters Darts

Location: Cheltenham Racecourse

Date: 21 February. Annual event


March 2020

The Festival™ featuring The Gold Cup

Location: Cheltenham Racecourse

Dates: 10 – 13 March 2020.  Annual event

(Day one - Champion Day, Day two – Ladies Day, Day three - St Patricks Day, Day four – Gold Cup).

Craft Festival Cheltenham

Location: Cheltenham Town Hall, Imperial Square, Cheltenham, Gl50 1QA

Date: 20 March. Annual event


April 2020

Cheltenham Wine Festival

Location: Pittville Pump Room, East Approach Drive, Cheltenham, GL52 3JE

Date: 4 April. Annual event

The April Meeting (Cheltenham races)

Location: Cheltenham Racecourse

Dates: 15 – 16 April. Annual event

Cheltenham Poetry Festival

Location: Various venues across Cheltenham

Dates: 16 – 25 April. Annual event (10th year)

Fresh Art Fair

Location: The Centaur, Cheltenham Racecourse

Dates: 24 – 26 April. Annual event


May 2020

Race Night featuring Hunter Chase Racing

Location: Cheltenham Racecourse

Date: 1 May.  Annual event

Cheltenham Jazz Festival

Location: Various venues across Cheltenham

Dates: 5 - 10 May. Annual event  

Cheltenham International Film Festival

Location: Various venues across Cheltenham

Dates: 23 - 31 May. Second year for this new festival

Cheltenham Children's Festival

Location: Cheltenham Town Hall

Date: May bank holiday Monday, 25 May.  Annual event (4th year)

Wychwood Music Festival

Location: Cheltenham Racecourse

Dates: 29 – 31 May. Annual event (16th year)

Cotswolds Festival of Steam

Location: GWSR train stations including Cheltenham Racecourse.

Dates: Late bank holiday weekend 23 – 25 May. Annual event

Cheltenham Festival of Performing Arts

Location: Cheltenham Town Hall

Dates: 5 – 17 May. Annual event


June 2020

Cheltenham Science Festival

Location: Across the town, main base Imperial Gardens

Dates: 2 - 7 June. Annual event (18th year)

Cheltenham Running Festival

Location: Cheltenham Racecourse

Date: 7 June. New event for 2020

Christian Arts Festival - Festival of the Stars

Location: Recreational Land, Whaddon Road, Whaddon, Cheltenham, Gloucestershire, GL52 5RA

Dates: 13 June. Annual event

Cheltenham Challenge

Location: Cheltenham Racecourse

Date: 14 June. Annual event

Cheltenham Food and Drink Festival

Location: Montpellier Gardens

Dates: 19 - 21 June. Annual event (12th year)

Cheltenham Balloon Fiesta

Location: Cheltenham Racecourse

Dates: 19 – 21 June. Annual event (2nd year)

Cheltenham Craft Beer and Cider Festival

Location: Various venues across town

Date: 6 June. Annual event


July 2020

Cheltenham Music Festival

Location: Various venues across town

Dates: 3 – 12 July. Annual event (76th year!)

Midsummer Fiesta

Location: Montpellier Gardens

Date: 4 July. Annual event (10+ years)

Bugatti Festival

Location: Prescott Hill Climb

Date: 4 July. Annual event

2000 Trees

Location: Upcote Farm, Withington

Dates: 9 – 11 July. Annual event

Cheltenham Cricket Festival

Location: Cheltenham College

Dates: 29 June – 9 July. Annual event (150th anniversary year!)

Open-Air Theatre Festival & Cinema Under The Stars

Location: Tuckwell Amphitheatre, Dean Close School, Cheltenham GL51 6EP

Dates: TBC. Annual event


August 2020

Cheltenham Cheese & Chilli Festival

Location: Sandford Park

Dates: TBC. Annual event


September 2020

Cheltenham Heritage Open Days

Locations: Various buildings throughout Cheltenham

Dates: 11 - 20 September. Annual nationwide event

Cheltenham Wellbeing Festival

Location: Various venues across town

Dates: TBC. Annual event (2nd year)

Cheltenham Paint Festival

Location: Various walls & venues throughout Cheltenham 

Dates: TBC. Annual event

Jason Donovan Concert

Location: The Centaur, Cheltenham Racecourse

Date: 16 September. One off event


October 2020

Cheltenham Literature Festival

Location: Montpellier Gardens and various venues around town

Dates: 2 – 11 October 2020.  Annual event (71st year!)


November 2020

The Cheltenham Beer Festival

Location: Cheltenham Ladies College

Dates: 1 - 2 Nov. Annual event

The Gin to My Tonic Festival

Location: Cheltenham Town Hall

Date: 2 November. Annual event (2nd year)

Christmas Lights Switch On

Location: Cheltenham Town Centre

Date: 21 November. Annual event


December 2020

Cheltenham late night shopping

Location: Select shops throughout Cheltenham town centre

Date: TBC


Other major Cheltenham events that are yet to be confirmed for 2020 –

Cheltenham Festival of Cycling

Street Chilli Fiesta

Related

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Prescott Hill Climb

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Wychwood Festival
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Cheltenham Festival of Performing Arts 2020 dates: 5 - 16 May 2020 The 94th Cheltenham Festival of Performing Arts will be packed with performances in music, dance and drama by children from local schools, theatre clubs, dance schools, music clubs etc. There is something different every day from ballet and tap to piano and strings, Shakespeare and poetry. Adults also provide music and drama performances including the Choral Day on the last Saturday. With tickets valid for the whole day you can go to as many performances as you like or become a Friend of the Festival for entry to the whole 13 days.

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2020 Cheltenham Craft Beer and Cider Festival Date - Saturday 6 June 2020 A wonderful family and dog friendly Beer Festival, with outdoor stage and music, run by the Cheltenham Friends of the Samaritans.  Get your summer off to the perfect start by attending the 15th Cheltenham Craft Beer and Cider Festival.

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2000 Trees Festival 2020 dates: 9 - 11 July 2020 The multi-award-winning 2000trees festival is a 3 day extravaganza set in the stunning Cotswold Hills. You’ll get 3 nights camping, a friendly, intimate atmosphere plus amazing food and locally produced ciders, ales & lagers. Described as one of the friendliest festivals you’ll ever go to, it’s perfect to attend with a group of mates or on your own, because you’re guaranteed to make new friends.

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: Cheltenham Cricket Festival 2020 dates: 29 June - 9 July 2020 The Cheltenham Cricket Festival is one of the most loved events in the social and sporting calendar. The idyllic setting of Cheltenham College provides the perfect backdrop for cricket at the height of summer. Gloucestershire have been playing in the stunning grounds of Cheltenham College for over 140 years, making this the world’s longest running cricket festival on an outfield.  The ground’s idyllic setting has provided a perfect backdrop for the Festival throughout its history, a great attraction for cricket fans, new supporters and big cricketing stars. Whether you’re an avid cricket fan or a first timer, the festival is the perfect opportunity to entertain clients, trea

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