Halloween is Saturday 31 October, the day after half term. The Wilson's trail runs 24 October to 1 November, its £10 party is on the 30th. Dunkertons goes 18+.

Halloween 2026 falls on Saturday 31 October, the day after Gloucestershire’s October half term ends. So most of Cheltenham’s Halloween events are spread through the half-term week rather than on the night, and the busiest day is Friday 30 October.

The quick answer

  • For families: the Halloween Trail at The Wilson, daily from 24 October to 1 November, 10am to 5pm, and its £10 Halloween Party on Friday 30 October at 2pm
  • For little ones: Halloween Tots at The Wilson on Tuesday 27 October, £5, and Spooky Pants at Dunkertons on the 28th and 30th, £10
  • For adults: Dunkertons’ 18+ Halloween party with Tux Fizz on Friday 30 October, £15, or the Playhouse’s Drag Music Quiz Halloween Special the same night, £10
  • Sold out already: the Everyman’s Ghosts and Superstitions tours on 30 and 31 October

Every date below was read from the organiser’s own listing on 1 October 2026.

Half term dates

For council-run schools in Gloucestershire, the October half term is Monday 26 to Friday 30 October 2026. Cheltenham College and Cheltenham Ladies’ College break earlier, from Friday 16 October. The full table, including Pate’s and Dean Close, is on our Gloucestershire school term dates page.

The Wilson: a trail, a party and a tots session

The Wilson on Clarence Street reopens after its refit on Friday 23 October, and Halloween is its first week back. All three events are listed by The Cheltenham Trust, which runs the museum.

Halloween Trail, Saturday 24 October to Sunday 1 November. Pick up a trail map and hunt the galleries for “creepy creatures, mysterious objects and hidden surprises”, with a Halloween treat at the end. It runs during gallery hours, 10am to 5pm, and a ticket can be used at any time of day. Tickets are sold online or from the cafe on arrival. The Trust does not print the price on the listing, and some online bookings carry a one-off £2.50 transaction fee (The Cheltenham Trust).

Halloween Tots Spooktakular, Tuesday 27 October, 10.30am, £5. An hour with Drama Tots: a Halloween drama adventure, a disco, bubbles, obstacles and a Halloween hunt. It is recommended for 18 months to 5 years, costumes are encouraged and an adult must take part throughout (The Cheltenham Trust).

Halloween Party, Friday 30 October, 2pm, £10. A craft party in costume. The ticket covers the craft activities, glitter tattoos, the museum’s Into The Night experience, a trick or treat sweet and 20% off in the cafe. It is not a drop-off session: children must stay with their adults, and adults do not need a ticket (The Cheltenham Trust).

The same week the Wilson runs free curator-led tours at 3pm from Tuesday 27 to Friday 30 October (places must be reserved), and Creative Explorers, an artist-led holiday club for ages 5 to 11, on Wednesday 28 October at 10am, £20 (The Cheltenham Trust).

Dunkertons: painting, dancing and an adults-only party

Dunkertons, at Dowdeswell Park on London Road (GL52 6UT, in Charlton Kings), has the busiest half-term programme in town. All of these are on its events page.

  • Spooky Pants, Wednesday 28 and Friday 30 October, £10. Funky Pants’ music and dance sessions for ages 0 to 5, opened up to last year’s leavers for a “Reception Reunion”. Halloween fancy dress is encouraged. Booking is through Funky Pants’ own Bookwhen page.
  • Children’s Halloween Painting Workshop, Thursday 29 October, 10.30am to 12pm, from £13. Paint Pot Parties run a haunted house canvas session for ages 6 and over, materials included. Adults do not need a ticket but must stay in the taproom. It is in a marquee, so dress for the weather. Tickets are sold by Paint Pot Parties through Eventbrite.
  • Halloween Party with Tux Fizz Live, Friday 30 October, doors 6.30pm, band 7.30pm, £15. Adults only, with ID checked against the booking name. Tickets are non-refundable and non-transferable, and Dunkertons warns that tickets offered in social media comments are fake. Parking is limited to the overflow car park; it suggests taxis or car sharing.
  • Decoupage Skull Painting, Monday 26 October, 7pm to 9pm, from £28, adults only, booked through Paint Pot Parties.

Not Halloween, but in the same half-term week at Dunkertons: Cotswold Children’s Parties’ autumn show for ages 3 to 7 on Monday 26 October, 10am to 11am, £10, and the Dinosaur, Wildlife and Education Centre’s animal show on Tuesday 27 October, £10.

Theatre and screen

  • Halloween in Concert, Sunday 18 October, 7.30pm, Everyman Theatre. A live band playing Halloween hits from Monster Mash to Thriller, with a prize for the best costume. It falls a week before half term (Everyman Theatre).
  • Dracula: The Panto!, Tuesday 27 October, 2.30pm and 7pm, Everyman Studio. Two performers, a Dame and a naughty Count (Everyman Theatre).
  • Ghosts and Superstitions of the Everyman Theatre and Opera House, Friday 30 and Saturday 31 October, 11am. Both dates were sold out on 1 October (Everyman Theatre).
  • Drag Music Quiz: Halloween Special, Friday 30 October, 7.30pm, Cheltenham Playhouse, Bath Road, £10. Hosted by Latina Ballroom and Eva More (Cheltenham Playhouse).

For younger children who would rather skip the spooky stuff, the half-term week also has The Three Little Pigs at the Playhouse on Thursday 29 October at 11.30am, £13, and Sea Legs’ puppet show Three Little Pirate Pigs at the Everyman on Friday 30 October at 11.30am and 2.30pm. The rest of the month is on our what’s on in Cheltenham page.

Racing on the first Saturday

The jump season opens at Cheltenham Racecourse with The William Hill Showcase on Friday 23 and Saturday 24 October. The Saturday is the first day of half term, and under-18s race free, though they need a booked ticket. Gates open at 11.15am (The Jockey Club). Every winter fixture is on our racecourse this winter page.

What we could not confirm

  • Halloween night itself. None of the organisers above has a Halloween event on the evening of Saturday 31 October. The only Halloween listing that day is the Everyman’s sold-out 11am tour.
  • GWSR “Spooky Specials”. Visit Cheltenham lists a Halloween steam train on 31 October, billed as the railway’s first. On 1 October the Gloucestershire Warwickshire Railway’s own website and booking site carried no page, times or tickets for it, so we have not listed it. We will add it when the railway does.
  • Cheltenham Borough Council has announced no Halloween event of its own.

The fireworks follow a few days later: Dunkertons on 3 November, the cricket club on the 6th and the racecourse on the 7th. See Cheltenham fireworks.

Getting there

The Wilson, the Everyman and the Playhouse are all in or near the town centre. Council car park tariffs, including Saturday rates, are on our parking in Cheltenham page, and any closures that week will be on Cheltenham roadworks and travel. Dunkertons is on the A40 London Road in Charlton Kings, and asks evening visitors to use its overflow car park.

Sources