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: 112

, 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 The Lion, the Witch and the Wardrobe to your Itinerary

    The Lion, the Witch and the Wardrobe

    Type

    Type:

    Theatre

    Cheltenham

    Dates

    From:
    2 May 2024to5 May 2024Open 19:30 -
    From:
    4 May 2024Open 14:00 -

    Take your time, open the door, and enter a world that wasn't there before. There's music from far away, snow falling near, and plainly there's magic at work here.

  2. Add "The Speakeasy" - Cheltenham Jazz Festival at The Frog and Fiddle to your Itinerary

    "The Speakeasy" - Cheltenham Jazz Festival at The Frog and Fiddle

    Type

    Type:

    Free Event

    Cheltenham

    Dates

    From:
    3 May 2024Open 19:30 - 23:00

    Free Entry Jazz Festival Show

  3. Add Josienne Clarke to your Itinerary

    Josienne Clarke

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    3 May 2024Open 19:30 - 10:20

    Indie-folk singer, songwriter, guitarist, and producer Josienne Clarke is often said to draw on traditional British folk inspirations, but is a thoroughly modern, multifaceted artist who follows her own compass.

  4. Add Drag Brunch at The Alchemist to your Itinerary

    Drag Brunch at The Alchemist

    Type

    Type:

    Food and Drink

    Henrietta Street, Cheltenham

    Dates

    From:
    4 May 2024Open 12:30 - 15:00

    Enjoy performances from this iconic drag duo as you sip equally fierce cocktails with a delicious brunch dish included.

  5. 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.

  6. Add My John Lewis Members' Week to your Itinerary

    My John Lewis Members' Week

    Type

    Type:

    Free Event

    123 High Street, Cheltenham

    Dates

    From:
    4 May 2024to5 May 2024Various Opening Times

    Join the John Lewis team in store for a weekend of events and experiences.

  7. Add Party In The Park, May Bank Holiday to your Itinerary

    Party In The Park, May Bank Holiday

    Type

    Type:

    Family

    Cheltenham

    Dates

    From:
    4 May 2024to6 May 2024Various Opening Times

    There's no better way to spend a sunny May Bank Holiday Weekend in the Cotswolds than with friends, family, farm animals and good music.

  8. Add The Flaming Alligators at Dunkertons - Jazz Festival Weekend to your Itinerary

    The Flaming Alligators at Dunkertons - Jazz Festival Weekend

    Type

    Type:

    Free Event

    Charlton Kings, Cheltenham

    Dates

    From:
    4 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.

  9. Add "Fusion Rocks" - Cheltenham Jazz Festival at The Frog and Fiddle to your Itinerary

    "Fusion Rocks" - Cheltenham Jazz Festival at The Frog and Fiddle

    Type

    Type:

    Free Event

    Cheltenham

    Dates

    From:
    4 May 2024Open 19:30 - 23:00

    Jazz Infused Rock

  10. Add The Music of Star Wars to your Itinerary

    The Music of Star Wars

    Type

    Type:

    Concert

    Evesham Rd, Cheltenham

    Dates

    From:
    4 May 2024Open 19:30 - 21:40

    Strap in as The Studio Orchestra take you on a hyperdrive adventure through the music of Star Wars.

  11. Add Triple Sec Septet to your Itinerary

    Triple Sec Septet

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    4 May 2024Open 10:30 - 13:00

    Jazz in the Minster

Statues