October 2025 - What's On Cheltenham Events

There is simply nowhere better to spend the autumn in the UK than Cheltenham, The Festival Town. The leaves are turning colour and our Regency spa town looks truly magical.

October will once again be an action-packed month with Cheltenham Literature Festival hosting 10 days of fascinating discussion and unforgettable memories. The first races of the season will also take place at Cheltenham Racecourse - The Showcase plus lots of live performances and markets. Scroll down for more October events in Cheltenham.

The half-term holiday towards the end of October will be filled with spooky Halloween fun, including Cotswold Farm Park’s pumpkin patch.

For help planning the rest of your year check out our Cheltenham Festivals & Major Events Guide. Plan your staycation in our Regency town with the help of these useful Cheltenham Staycation Ideas and Cheltenham Weekend Itineraries.

Event organisers - You can add your event for free to our what's on guide here.