A collage of images showcasing October events in Cheltenham awell as the town's Autumn colours

October 2025 - What's On Cheltenham Events

Highlights

Cheltenham Literature Festival Free Events

Cheltenham Literature Festival Free Events

With more than one hundred free talks, performances and workshops taking place across the ten days…

Cheltenham Literature Festival

Cheltenham Literature Festival

Cheltenham Literature Festival, 10-19 October, promises a feast for the mind. As the world’s…

The Showcase at Cheltenham Racecourse

The Showcase

The Showcase raises the curtain to the 2025/26 Cheltenham season, once again, the thundering…

PizzaExpress exterior

PizzaExpress Cheltenham

Cheltenham Pizza Express is located at The Brewery Quarter Shopping Centre - the home of shopping,…

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Number of results: 28

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Featured Events

  1. Add Cheltenham Literature Festival to your Itinerary

    Cheltenham Literature Festival

    Type

    Type:

    Festival

    Cheltenham

    Dates

    From:
    10 Oct 2025to19 Oct 2025

    Cheltenham Literature Festival, 10-19 October, promises a feast for the mind. As the world’s longest-running literature festival, the annual event leads the way in celebrating the written and spoken word, presenting the best new voices in fiction…

  2. Add Cheltenham Farmers Market to your Itinerary

    Cheltenham Farmers Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    10 Oct 2025
    From:
    24 Oct 2025

    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...

  3. Add Cheltenham Craft Market to your Itinerary

    Cheltenham Craft Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    18 Oct 2025

    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.

  4. Add The Showcase to your Itinerary

    The Showcase

    Type

    Type:

    Horse Racing

    Cheltenham

    Dates

    From:
    24 Oct 2025to25 Oct 2025

    The Showcase raises the curtain to the 2025/26 Cheltenham season, once again, the thundering hooves, eager participants and excited fans will return to the Home of Jump Racing on Friday 24 and Saturday 25 October 2025. 

  5. Add The Suffolks Sunday Market to your Itinerary

    The Suffolks Sunday Market

    Type

    Type:

    Market

    Cheltenham

    Dates

    From:
    26 Oct 2025Open 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.

Ongoing Events

  1. Add Beginners Dry Stone Walling Courses at Notgrove to your Itinerary

    Beginners Dry Stone Walling Courses at Notgrove

    Type

    Type:

    Workshop

    Notgrove, Cheltenham

    Dates

    From:
    2 Oct 2025to3 Oct 2025Open 09:00 - 16:30
    From:
    11 Oct 2025to12 Oct 2025Open 09:00 - 16:30

    Dry stone walling courses for beginners at Notgrove suitable for anyone 16 years and older. Run by DSWA instructor with years of experience, Richard Gray at Notgrove over two days. Accommodation at Notgrove available on site. Price is £199 pp.

  2. Add Botanist Musical Bingo to your Itinerary

    Botanist Musical Bingo

    Type

    Type:

    Competition/Game

    Henrietta Street, Cheltenham

    Dates

    From:
    2 Oct 2025Open 20:00 - 22:00

    Eyes Down, Listen Up! One musician, three chances to win. Bingo re-imagined. The first Thursday of every month.

  3. Add Autumn Yoga and Wellness Retreat to your Itinerary

    Autumn Yoga and Wellness Retreat

    Type

    Type:

    Health & Wellbeing

    Notgrove, Cheltenham

    Dates

    From:
    3 Oct 2025to5 Oct 2025Open 15:00 - 12:00

    Autumn Weekend Retreat: 3rd to 5th October 2025 with Sadie Brewin. Suitable for all abilities. Price is all inclusive including your pod, home cooked food and all classes. You'll leave feeling relaxed and rejuvenated.

  4. Add Cheltenham Lido Swim Challenge to your Itinerary

    Cheltenham Lido Swim Challenge

    Type

    Type:

    Swimming

    Cheltenham

    Dates

    From:
    4 Oct 2025Open 07:30 - 14:00

    Set yourself a goal this summer and complete the Cheltenham Lido swim challenge!

  5. Add Cheltenham Literature Festival Free Events to your Itinerary

    Cheltenham Literature Festival Free Events

    Type

    Type:

    Literature

    Cheltenham

    Dates

    From:
    10 Oct 2025to19 Oct 2025

    With more than one hundred free talks, performances and workshops taking place across the ten days of the Festival.

  6. Add 80's Night at Leonardo Hotel Cheltenham to your Itinerary

    80's Night at Leonardo Hotel Cheltenham

    Type

    Type:

    Music

    Cheltenham

    Dates

    From:
    10 Oct 2025Open 18:30 - 23:50

    Join the team at Leonardo Hotel Cheltenham for an 80's Night which is guaranteed to be an unforgettable evening!

  7. Add Cheltenham Antiques & Vintage Market to your Itinerary

    Cheltenham Antiques & Vintage Market

    Type

    Type:

    Antiques

    Cheltenham

    Dates

    From:
    11 Oct 2025

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

  8. Add Craft Market at The Tithe Barn to your Itinerary

    Craft Market at The Tithe Barn

    Type

    Type:

    Market

    Bishops Cleeve, Cheltenham

    Dates

    From:
    18 Oct 2025Open 11:00 - 15:00

    Craft market with incredible local stallholders.

  9. Add Dunkertons Comedy Nights to your Itinerary

    Dunkertons Comedy Nights

    Type

    Type:

    Comedy

    Charlton Kings, Cheltenham

    Dates

    From:
    26 Oct 2025Open 18:00 - 20:00

    Visit Dunkertons Park on Sunday evenings, once a month, for a lively evening with outstanding comedy, unreal street-food, and award-winning organic cider. Hosted in a stunning & welcoming venue.

  10. Add Steak Day at Tailors to your Itinerary

    Steak Day at Tailors

    Type

    Type:

    Food and Drink

    Cheltenham

    Dates

    From:
    19 June 2024to15 Oct 2025Open 12:00 - 21:00

    Steak Day at Tailor's. Starting Wednesday 19th June, every Wednesday 12pm-9pm

  11. Add Turning The Pages to your Itinerary

    Turning The Pages

    Type

    Type:

    Historical

    Pittville, Cheltenham

    Dates

    From:
    9 July 2024to31 Dec 2025Open 10:00 - 16:00

    Explore Holst's manuscripts on innovative Turning The Pages software.

  12. Add Weekend brunch at The Alchemist to your Itinerary

    Weekend brunch at The Alchemist

    Type

    Type:

    Food and Drink

    Henrietta Street, Cheltenham

    Dates

    From:
    10 Sept 2024to31 Dec 2025Various Opening Times

    Good time revellers, it’s time to get your brunch on. A brunch dish and 3 cocktails – upgrade to bottomless drinks for £10* extra. Available Saturday from 10am & Sunday from 11am.

  13. Add PizzaExpress Cheltenham to your Itinerary

    PizzaExpress Cheltenham

    Type

    Type:

    Italian

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Cheltenham Pizza Express is located at The Brewery Quarter Shopping Centre - the home of shopping, dining and leisure in Cheltenham.

  14. Add Cineworld movies for juniors to your Itinerary

    Cineworld movies for juniors

    Type

    Type:

    Days Out

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025Various Opening Times

    Want to introduce your children to the exciting world of cinema? Then Movies For Juniors is the perfect place to start.

  15. Add Masterclasses at Brewhouse & Kitchen to your Itinerary

    Masterclasses at Brewhouse & Kitchen

    Type

    Type:

    Food and Drink

    Cheltenham

    Dates

    From:
    1 Jan 2025to31 Dec 2025

    Join the Brewhouse & Kitchen team for one of their in-house masterclasses. Learn the ins and outs of Gin, Beer or Rum or discover the brewing process behind the pubs fantastic range of ales.

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