It's that time to wrap up warm again as autumn officially arrives.  The fall is a particularly pretty time to visit Cheltenham, with our tree lined streets turning vibrant shades of orange and literature fans from near and far flocking to our Regency town to experience the world’s oldest literature festival. 

Of course it’s also the spooky season with many Halloween themed events taking place across the town from pumpkin picking to ghost tours.   Here is our round up of the best things to do in Cheltenham this October…

Unmissable events October…

70th anniversary Cheltenham Literature Festival

Dates: 4 – 13 October

Location: Montpellier Gardens, Cheltenham, Gloucestershire, Gl50 1UW (+ various ticketed venues)

Every autumn for ten days Cheltenham is transformed into a literary lover’s dream with over 900 of the world's best writers, brightest thinkers and inspiring performers taking part in once-in-a-lifetime conversations, critical debate and literary revelry. This year the theme of the festival is 7 At 70 to celebrate the festivals 70th birthday. 

There are still some tickets available to select events, plus there's a whole programme of free activities to enjoy including the Around Town events such as the Elmer and Friends Trail, the Lit Crawl, family fun in the Festival Village and stimulating talks, entertainment and music in The Huddle in the Feast Café.  

Check out our exclusive top tips for making the most of Cheltenham Literature Festival by Head of Programming. And our guide to the best places to eat during Cheltenham Literature Festival. 

Full event details.

Buy tickets.

The Showcase

Dates: 25 - 26 October

Location: Cheltenham Racecourse

The Home of Jump racing kicks off the season in style with The Showcase. The exciting two-day meeting sees a host of new racing recruits join the ranks - from trainers and jockeys to future equine stars and sets the tone for what's to come, leading all the way to The Festival™ presented by Magners in March 2020. 

New for 2019 is Cheltoberfest, a beer themed event with live music which will take place in The Centaur across both days of The Showcase.

Halloween events 

Pumpkin Picking & Halloween Land 

Dates: 21 - 24 October for Pumpkin Picking & 25 October - 3 November for Halloween Land

Location: Cotswold Farm Park

Our popular attraction, Cotswold Farm Park, is promising cauldrons of spooky fun this October.  Pick a pumpkin fresh from the farm, get crafty and choose a fearsome face painting design!

Enchanted Sudeley

Dates: 26 - 3 November

Location: Sudeley Castle

Find enchanted scenes hidden around the castle to discover the stories of the Brothers Grimm. Follow a magical fairy tale trail through Sudeley Castle and its gardens, discovering scenes from a host of famous stories from Grimm's fairy tales, including Snow White, Rapunzel and Sleeping Beauty.

Ghost Tours

Dates: Various throughout the year

Location: Guided walks available around Cheltenham and Prestbury

These spooky tours are not for the faint of heart, but will provide food for thought as well as sending a few chills down your spine!  

Other top picks:

Starlight Hike. A night to remember.

Date: 19 October

Location: St Edwards Prep School

An annual event raising vital funds for Sue Ryder Leckhampton Court Hospice.  
Expect the a party atmosphere and entertainment as you walk 10k under the stars together, great live music from the fabulous Rock Choir, glowing merchandise for sale and refreshments also available.

Autumn Wildlife Trail

Date: 1 Sept – 25 Oct

Location: Sudeley Castle

Get closer to British wildlife as you follow a footprint trail around the beautiful vibrant gardens of Sudeley Castle.

Children can follow a new autumnal wildlife footprint trail around the grounds, finding out about some of the creatures that call our countryside home.

Misshapes: The Making of Tatty Devine

Date: 3 Sept – 3 Nov

Location: The Wilson - Cheltenham Art Gallery & Museum

We are proud that our local art gallery is the first regional venue on a UK-wide tour to showcase this exhibition.  Pop by to over 100 pieces from the Tatty Devine’s archive including unique statement jewellery.  

Holst Birthday Concert

Date: 5 Oct

Location: St Andrews Church

This year's annual Holst Birthday Concert will be performed by the superb Cheltenham Chamber Orchestra (conductor Timothy Carey) who will be joined by solo viola player Ana Teresa Alves.

Fine Food & Drink Market

Date: 5 October

Location: The Promenade outside Cavendish House

Supporting artisans in the rural economy, Cheltenham Fine Food & Drink Market brings together local producers and purveyors of local delicacies and handmade delights. Whether you're a fudge fanatic or a pie pursuer, there's something on offer; fudge, pies, cheese, wine and everything in between. 

Cheltenham Farmers Market

Dates: 11 October & 25 October

Location: Promenade House, Cheltenham, Gloucestershire, GL50 1PJ

Stroll along the stalls selling a range of produce including various meats and charcuterie, fruit and vegetables, desserts, preserves and pickles, cakes, bread, cheese and plants.

Christmas Gift Fair

Date: 17 - 18 October

Location: The Centaur, Cheltenham Racecourse

Get your Christmas shopping done early with this fair that has more than 150 retailers under one roof selling an exclusive selection of stylish gifts, festive food, stocking fillers, fabulous fashion, unique home décor, art, great games and toys plus jewellery and handbags.

For a full list of things to do in Cheltenham check out our comprehensive What's On Guide.


Cheltenham Literature Festival
Cheltenham Literature Festival

The world’s first literature festival still leads the way in celebrating the written and spoken word, presenting the best new voices in fiction and poetry alongside literary greats and high-profile speakers, while inspiring over 9,000 school children with a love of books. All set here in Cheltenham, The Festival Town, with free pop-up events galore and festivities continuing late into the night.



Nobody has commented on this post yet, why not send us your thoughts and be the first?

Leave a Reply