2020 was a year that most of us would rather forget. To give you some things to look forward to we've created a list of the unmissable Cheltenham events in 2021. 

Proud to be known as The Festival Town, our Regency town is home to 35+ truly world-class festivals / major events a year which provide the perfect opportunity for shared experiences and life affirming moments with family and friends.

Many of the events below are annual events, some are a one-off.  We've clearly highlighted these so you can make plans for future visits to Cheltenham. For more comprehensive information check out our Cheltenham 2021 - Festivals and Major Events Guide.

** Due to the ongoing COVID pandemic we anticipate that Cheltenham events and festivals will continue to adapt / change over the year. We will endeavour to keep this guide up to date however, we recommend that you click through to the official event website for the latest information prior to travelling or booking accommodation. **

Collage of Cheltenham 2021 unmissable events

March 2021

The Festival™ featuring The Gold Cup

Location: Cheltenham Racecourse. This event may take place behind closed doors due to the national lockdown.

Dates: 16 – 19 March.  Annual event

(Day one - Champion Day, Day two – Ladies Day, Day three - St Patrick’s Thursday, Day four – Cheltenham Gold Cup).


April 2021

Cheltenham Comedy Drive-In

Location: Cheltenham Racecourse

Dates: 9 – 11 April. New event.

Parking Lot Social Drive-In Easter Festival

Location: Southham Car Boot Site (next to Cheltenham Racecourse)

Dates: 12-13 April. New event. 

The April Meeting

Location: Cheltenham Racecourse

Dates: 14 – 15 April. Annual event

Cheltenham Poetry Festival

Location: Not running a physical festival this year 

Dates: Online one-off events throughout year.

Race Night featuring Hunter Chase Racing

Location: Cheltenham Racecourse

Date: 30 April.  Annual event


May 2021

Cheltenham Jazz Festival

Location: A digital only festival for 2021

Dates: 1 – 2 May. Annual event  

Cheltenham Challenge

Location: Virtual event for 2021

Dates: 22 & 23 May. Annual event.

Cheltenham Festival of Performing Arts

Location: Pittville Pump Room.

Dates: 23 May - 3 June. Annual event,  Cheltenham’s oldest festival.

Cheltenham International Film Festival

Location: Various venues across Cheltenham

Dates: 24 May – 5 June. Annual event incorporating for 1st year Youth Festival and Online Festival.

Cotswolds Festival of Steam

Location: GWSR train stations including Cheltenham Racecourse.

Dates: Sadly not taking place in 2021

Cheltenham Children's Festival

Location: Cheltenham Town Hall

Date: TBC - 31 May. No formal decision has been made regarding whether this event will take place in 2021.

Kingfisher Trail – Cotswolds 2021

Location: 21 locations throughout the Cotswolds including Cheltenham

Dates: 31 May – 17 October


June 2021

Wychwood Music Festival

Location: Cheltenham Racecourse

Dates:  4 – 6 June. Annual event (16th year).

Cheltenham Science Festival

Location: Across the town, main base Imperial Gardens

Dates: 10 - 13 June.  Annual  event.

Cheltenham Craft Beer and Cider Festival

Location: The Old Patesians Rugby Club

Date: 12 June.  Annual event (15th year).

Cheltenham Running Festival

Location: Cheltenham Racecourse

Date: 13 June. New event for 2021.

Cheltenham Balloon Fiesta

Location: Cheltenham Racecourse

Dates: 25 – 27 June. Annual event (2nd year)

Cheltenham Food and Drink Festival

Location: Montpellier Gardens

Dates: 25 - 27 June. Annual event (12th year)

Prescott Bike Festival

Location: Prescott Hill Climb, Gotherington, Cheltenham

Dates: 26 - 27 June. Annual event. Preview day Sat, main show Sun.


July 2021

Cheltenham Music Festival

Location: Various venues across town

Dates: 2 – 9 July. Annual event (77th year)

Cheltenham Cricket Festival

Location: Cheltenham College Grounds

Dates: 9 & 16 July. Annual event (the world's oldest cricket festival)

2000 Trees

Location: Upcote Farm, Withington

Dates: 8 – 10 July.  Annual event

Midsummer Fiesta

Date: Not taking place in 2021


August 2021

Fresh Art Fair

Location: The Centaur, Cheltenham Racecourse

Dates: 5 - 8 August. Annual event.

Craft Festival Cheltenham

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

New date: 13 - 15 August.


September 2021

Cheltenham Heritage Open Days

Locations: Various places of historical interest throughout Cheltenham

Dates: 10 - 19 September. Annual nationwide event.

International Beer Festival

Location – Cheltenham Town Hall

Date: 11 September. New event for 2021.

Cheltenham Paint Festival

Location: Various walls & venues throughout Cheltenham 

Dates: 10 - 12 September. Annual event.

Gin to My Tonic Festival

Location: Cheltenham Town Hall

Date: 25 September 2021. Annual  event.


October 2021

Cheltenham Literature Festival

Location: Montpellier Gardens and various venues around town

Dates: 8 – 17 October.  Annual event, the world’s oldest literature festival!

Jason Donovan Concert

Location: The Centaur, Cheltenham Racecourse

Date: 19 October.  One off event.

The Showcase

Location: Cheltenham Racecourse

Dates: 22 - 23 October. Annual event.

Cheltenham Wine Festival

Location: Pittville Pump Room

New date: 30 October. Annual event


November 2021

The November Meeting

Location: Cheltenham Racecourse

Dates: 12 - 14 November. Annual event.

Jack and the Beanstalk – Panto

Location: Everyman Theatre

Dates: 26 Nov - 9 Jan

Christmas Lights Switch On

Location: Cheltenham Town Centre

Date: November - date TBC. Annual event

Cheltenham Ice Rink

Location: Imperial Gardens

Dates: November to January. Dates TBC.


December 2021

Cheltenham Ice Rink

Location: Imperial Gardens

Dates: November to January. Dates TBC.


January 2022

New Year’s Day Races 

Location: Cheltenham Racecourse

Date: 1 January 2022. Annual event

Festival Trials Day

Location: Cheltenham Racecourse

Date: 29 January 2022 - TBC. Annual event.


For more comprehensive information about all of these truly world-class events check out our Cheltenham 2021 - Festivals and Major Events Guide.

We feature 1,500+ events on this website every year so we recommend you also check our Cheltenham What's On Guide and Cheltenham 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 in 2021 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 even Cheltenham campsites. Our We're Good To Go guide lists the Cheltenham venues following industry and Government COVID-19 guidance on cleanliness, staff training and social distancing measures. 

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

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