A collage of Cheltenham happens in May

May 2024 - What's On Cheltenham Events

Highlights

Cotswold Festival of Steam

Cotswold Festival of Steam

Remembering local scenes, this year's GWSR Cotswold Festival of Steam is inspired by the huge…

Cheltenham Jazz Festival... around town free gigs

Cheltenham Jazz Festival... around town free gigs

Keep Thursday 2 May to Monday 6 May free to enjoy five days of free gigs on the Cheltenham Jazz…

Cheltenham Craft Market

Cheltenham Craft Market

Located along Cheltenham Promenade, the monthly Cheltenham Crafts Market brings together local…

Wychwood Festival Cheltenham Racecourse

Wychwood Festival

Wychwood is an annual summer family festival which takes place at Cheltenham Racecourse. Nominated…

Number of results:

Number of results: 104

, currently showing 1 to 20.

Featured Events

  1. Add Cheltenham Jazz Festival... around town free gigs to your Itinerary

    Cheltenham Jazz Festival... around town free gigs

    Type

    Type:

    Free

    Cheltenham

    Dates

    From:
    2 May 2024to6 May 2024

    Keep Thursday 2 May to Monday 6 May free to enjoy five days of free gigs on the Cheltenham Jazz Festival Free Stage in Montpellier Gardens and in Cheltenham’s streets, pubs and clubs.

  2. Add The Suffolks Sunday Market to your Itinerary

    The Suffolks Sunday Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    5 May 2024Open 11:00 - 16:00
    From:
    26 May 2024Open 11:00 - 16:00

    These fantastically-popular Street Fairs in the Suffolks are always great events. Whether it’s the May Bank Holiday or the Christmas Market, there’s always a lovely friendly atmosphere, great products on sale and lots of fun entertainment.

  3. Add Cheltenham Festival of Performing Arts to your Itinerary

    Cheltenham Festival of Performing Arts

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    9 May 2024to18 May 2024

    Cheltenham's oldest festival, set up in 1926! The annual Cheltenham Festival of Performing Arts is packed with performances in music, dance and drama by children from local schools, theatre groups, dance schools and music clubs...

  4. Add Cheltenham Farmers Market to your Itinerary

    Cheltenham Farmers Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    10 May 2024Open 09:00 - 14:00
    From:
    31 May 2024Open 09:00 - 14:00

    On the second and last Friday of every month stalls line Cheltenham Promenade selling a range of produce including various meats and charcuterie, fruit and vegetables, desserts, preserves and pickles, cakes, bread, cheese and plants...

  5. Add Cheltenham Antiques & Vintage Market to your Itinerary

    Cheltenham Antiques & Vintage Market

    Type

    Type:

    Antiques

    Cheltenham

    Dates

    From:
    11 May 2024

    Your opportunity to browse antiques, collectables, vintage products, home decor, porcelain, jewellery, furniture and art once a month along Cheltenham Promenade.  

  6. Add Cheltenham Craft Market to your Itinerary

    Cheltenham Craft Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    18 May 2024

    Located along Cheltenham Promenade, the monthly Cheltenham Crafts Market brings together local producers, craftspeople and artisans to create a market full of unique gifts, homeware and handmade goods.

  7. Add Cotswold Festival of Steam to your Itinerary

    Cotswold Festival of Steam

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    25 May 2024to27 May 2024

    Remembering local scenes, this year's GWSR Cotswold Festival of Steam is inspired by the huge variety on the railway network around Cheltenham and Gloucester during the heyday of steam.

  8. Add Prescott Historique to your Itinerary

    Prescott Historique

    Type

    Type:

    Sports

    Cheltenham

    Dates

    From:
    25 May 2024to26 May 2024Open 08:30 - 17:00

    Prescott Historique celebrates the history of British Hill Climbing, in the only Pre-war motorsport venue in Gloucestershire and this years event will showcase some of the most iconic competition cars ever.

  9. Add Wychwood Festival to your Itinerary

    Wychwood Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    31 May 2024to2 June 2024Various Opening Times

    Wychwood is an annual summer family festival which takes place at Cheltenham Racecourse. Nominated Best Family Festival at the UK Festival Awards, there is so much for all ages to enjoy and take part in. Wychwood Festival 2024 will take place 31 May…

Ongoing Events

  1. Add Live Music in The Ox Shed to your Itinerary

    Live Music in The Ox Shed

    Type

    Type:

    Free Event

    Guiting Power, Cheltenham

    Dates

    From:
    4 May 2024to5 May 2024
    From:
    11 May 2024
    From:
    18 May 2024
    From:
    25 May 2024
    From:
    29 May 2024

    Every Saturday evening Cotswold Farm Park are inviting you to dine and listen to live music from super-talented local artists from 5pm.

  2. Add Blues Shaker at Dunkertons - Jazz Festival Weekend to your Itinerary

    Blues Shaker at Dunkertons - Jazz Festival Weekend

    Type

    Type:

    Free Event

    Charlton Kings, Cheltenham

    Dates

    From:
    5 May 2024Open 13:00 - 15:00

    Feel the spirit of Cheltenham Jazz Festival with Dunkertons Park! Immerse yourself in a sensational array of musical performances all weekend long, with both free and ticketed sets.

  3. Add The Cinelli Brothers at Dunkertons - Jazz Festival Weekend to your Itinerary

    The Cinelli Brothers at Dunkertons - Jazz Festival Weekend

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    5 May 2024Open 19:00 -

    Feel the spirit of Cheltenham Jazz Festival with Dunkertons Park! Immerse yourself in a sensational array of musical performances all weekend long, with both free and ticketed sets.

  4. Add Julian Clary - A Fistful of Clary to your Itinerary

    Julian Clary - A Fistful of Clary

    Type

    Type:

    Comedy

    Cheltenham

    Dates

    From:
    5 May 2024Open 19:30 -

    Julian Clary, renowned homosexual and national trinket, is fixing to saddle up and head on out for his 2024 UK tour.

  5. Add Sunday Funday at The Frog & Fiddle to your Itinerary

    Sunday Funday at The Frog & Fiddle

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    5 May 2024Open 15:30 - 23:30

    15 Bands - 2 Stages - No Clashes

  6. Add The Alice Armstrong Band - Jazz Festival Weekend to your Itinerary

    The Alice Armstrong Band - Jazz Festival Weekend

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    6 May 2024Open 13:00 - 15:00

    Feel the spirit of Cheltenham Jazz Festival with Dunkertons Park! Immerse yourself in a sensational array of musical performances all weekend long, with both free and ticketed sets.

  7. Add Big Benhall Yard Sale to your Itinerary

    Big Benhall Yard Sale

    Type

    Type:

    Free Event

    Cheltenham

    Dates

    From:
    6 May 2024Open 10:00 - 13:00

    A map of all houses hosting a yard sale table will be published online and in print. Paper maps from Benhall Avenue businesses and some stalls.

  8. Add Legend: The Music of Bob Marley to your Itinerary

    Legend: The Music of Bob Marley

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    7 May 2024Open 19:30 -

    When you think reggae, there is only one name that comes to mind. The legend that was Bob Marley.

  9. Add Open Mic Night x Dunkertons - Free Drink for All Performers to your Itinerary

    Open Mic Night x Dunkertons - Free Drink for All Performers

    Type

    Type:

    Music

    Charlton Kings, Cheltenham

    Dates

    From:
    7 May 2024

    Unleash Your Talent at Dunkertons Open Mic Nights, Hosted by Flynn from DUKE.

  10. Add Bang the Drum at The Wilson to your Itinerary

    Bang the Drum at The Wilson

    Type

    Type:

    Children's

    Cheltenham

    Dates

    From:
    8 May 2024Open 10:00 -
    From:
    22 May 2024Open 10:00 -

    Bang the Drum is a new music making, rhythm and song session for little movers and shakers! Runs every other Wednesday, 10am.

  11. Add Quiz Night at Dunkertons to your Itinerary

    Quiz Night at Dunkertons

    Type

    Type:

    Family

    Charlton Kings, Cheltenham

    Dates

    From:
    8 May 2024Open 19:00 -
    From:
    15 May 2024Open 19:00 -

    Created and run by Quiz Master/theatrical genius - Joe, you'll be putting your brain cells to the test from start to finish! With loads of varied rounds everybody's in with a chance.

Statues