Ride the rails on special vintage steam trains

The Autumn Steam Gala brings three days of steam‑powered excitement, with unlimited rides behind visiting and home locomotives, running an enhanced timetable along the 10‑mile heritage line. Visitors can explore every station, enjoy Brake Van rides, discover restoration projects, and take in a range of talks and exhibits.

Autumn Steam Gala at The Watercress Line. 
Friday 2 - Sunday 4 October. 
📍Alresford

Celebrate Oktoberfest at South Downs Social

If you're swerving Sober October this year, head to South Downs Social on 2 October for a Bavarian-style celebration. You'll be guided through a tasting of six Oktoberfest beers from Munich’s famous breweries, followed by more beers, Oktoberfest music, and German bratwurst cooked up on the terrace grill.

Oktoberfest at South Downs Social. 
Friday 2 October.
📍Winchester city centre 

Watch a powerful dance set on a hospital ward

More than twenty years ago, her original masterpiece Lullaby took the theatre world by storm and won widespread critical acclaim. Now, internationally renowned choreographer Jasmin Vardimon reimagines and expands her landmark show. Against the backdrop of a cold, clinical hospital landscape, Vardimon explores the emotional highs and lows of human life

Jasmin Vardimon Dance: Lullaby at Theatre Royal Winchester. 
Tuesday 6 October. 
📍Winchester city centre 

See the new Ray Harryhausen exhibition

The story of a legendary animator who changed the course of film history, this special exhibition has been created for The Arc and drawn from the incredible archive of The Ray & Diana Harryhausen Foundation. Harryhausen’s innovation in stop motion has had a lasting effect on viewers and filmmakers alike.

Ray Harryhausen: Myth in Motion at The Gallery at The Arc. 
From Saturday 26 September. 
📍Winchester city centre 

Pick your own Halloween pumpkin

Whether you're looking for a wholesome October half-term activity or a cute photo opportunity, to carve them into haunting Halloween lanterns or make comforting autumnal pumpkin soups and pies, these are the pick-your-own pumpkin patches in and around Winchester to visit this year. Some have cafés on site and extra spooky things to do too, so you can make a full day of it.

📍Various locations 
Read more: PYO pumpkin patches in and near Winchester 

Go to a poetry open mic event

Winchester Poetry Festival returns this month for a day of poetry activities celebrating ‘performance and participation’. (Winchester Poetry Festival takes place every alternate year, returning in 2027. A shorter Winchester Poetry Day is planned for 2026.) The day will feature a performing poetry workshop, a celebration of The Hampshire Young Poets', a poetry open mic and more.

Winchester Poetry Day 2026 at The Arc. 
Saturday 10 October. 
📍Winchester city centre 

Hear Romesh Ranganathan's work-in-progress jokes

Laugh out loud (hopefully) at stand-up comedy from Romesh Ranganathan. He's in Winchester this month road testing new material ahead of his upcoming tour Romesh Ranganathan Will Change Your Life.

Romesh Ranganathan: Work In Progress at Theatre Royal Winchester. 
Saturday 10 October. 
📍Winchester city centre 

Spot signs of autumn on a Winchester walk or hike

Winchester district has so much glorious countryside to explore, and it looks especially lovely this time of year as the leaves are turning golden. From Winchester city centre, you can easily immerse yourself in autumnal colour with a wander around Winnall Moors or a walk up St Giles's Hill. You could enjoy a self-guided walk in the footsteps of poet John Keats from the city to St Cross, passing through the landscape which inspired his famous ode ‘To Autumn’. If you have little ones, see how much autumnal treasure you can find on the ground, from acorns and conkers to colourful leaves and seed pods. Make a full day of it with one of these pub walks near Winchester.

📍Various locations 
Read more: Walks in Winchester

Ride the big wheel at Alresford's annual street fair

For one autumnal evening only, Alresford's pretty Broad Street is transformed into a Michaelmas fun fair, which then disappears by the following morning. The historic fair has been popping up on the street for centuries. The usually peaceful spot is packed with stalls, loud music and flashing lights, while surprisingly big rides are squeezed in close to the Georgian homes that line the street. Younger children are encouraged to visit from 3pm, when the fair opens.

Image: E J Westmacott

Michaelmas Fun Fair in Alresford. 
Thursday 15 October. 
📍Alresford

Browse a selection of brilliant comics

The Winchester Comics Fair returns to the Nutshell for its fifth year to showcase the thriving indy UK comics scene. Come along and find comics, prints, postcards, and more from over 40 of the UKs best comics makers, artists, and writers.

Winchester Comics Fair at The Nutshell. 
Saturday 17 October. 
📍Winchester city centre 

Have a cosy Sunday lunch

Farewell BBQ season, October is all about lazy Sundays spent eating roast potatoes with bucket loads of gravy. Winchester has plenty of places to enjoy a comforting roast, whether you're a meat eater or after a plant-based Sunday lunch. Lainston House is the place to head if you like your roast dinner meaty and flame-grilled - their rustic restaurant The Wellhouse serves exclusively woodfired dishes. In Winchester city centre, you could visit The Wykeham Arms which serves a traditional Sunday roast in the shadow of Winchester Cathedral.

📍Various locations
Read more: Great places for Sunday roasts in and around Winchester 

Embrace spooky season at Hinton Ampner

The National Trust property near Winchester is going all out for autumn, with impressive pumpkin displays in the pretty kitchen garden and grounds from Saturday 17 October. There will also be Halloween half-term activities in the gardens between Saturday 17 October and Sunday 1 November.

Image: ©National Trust Images/Sophie Bolesworth

Pumpkin Displays at Hinton Ampner.
Saturday 17 October - Sunday 1 November. 
📍near Cheriton  

Watch a movie in Winchester's secret cinema

Head to Cabinet Rooms this month to watch one of the films they're screening. The cosy café bar has a secret screening room downstairs with room for 10 cinemagoers. This October they are showing a great selection of films to mark Black History Month, as well as some spooky and scary ones for Halloween. Sign up to their mailing list or ask in the café to book.

Cabinet Rooms. 
📍Winchester city centre 

Dance at a grown-up disco

Discos for Grown Ups is taking over beautiful Bapsy Hall at Winchester's Guildhall for an afternoon and night of 70s disco, 80s pop and 90s dance classics. There people in disco finery (the dress code is Disco Glamour) and the likes of Donna Summer, Chaka Khan, Abba and Faithless to dance away to. Come in the afternoon for a silent disco, or in the evening for something louder.

Discos for Grown Ups at The Guildhall.
Saturday 17 October. 
📍Winchester city centre

Graduate from Broomstick Academy

Droxford Pumpkin Patch returns for 2026 with pumpkin picking and carving, face painting, potion making and more. There's a spooky Halloween disco to dance at, Bale Mountain to climb and Broomstick Academy to graduate from. You can also meet and feed the resident sheep, settle down for a movie at the Strawbale Cinema, visit the café or refuel with a wood-fired pizza.

Droxford Pumpkin Patch.
Friday 23 October - Saturday 31 November.
📍near Bishop's Waltham

Make mega October half-term memories in Winchester

Schools out, ghouls out. From spooky trails to steam trains, look no further for October half-term events and family days out across Winchester district. It's October half-term (Saturday 24 October - Sunday 1 November 2026) in Winchester and we have some great ideas to keep you and your little ones busy over the school break. There's plenty to do if you want to get into the Halloween spirit, from ghost stories to pumpkin patches, as well as loads on if you'd rather swerve anything spooky and spend October half-term soaking up autumn in Winchester instead.

Read more: October half-term in Winchester

Get creative at a sociable painting evening

Paint a canvas or a Halloween decoration at a relaxed evening at The Square. Paint with Pals will provide all the art materials, as well as encouragement and advice. You just have to provide the creativity, though there's no pressure and no artistic experience necessary!

Paint with Pals Halloween Special at The Square. 
Saturday 24 October. 
📍Winchester city centre 

Visit the Witches of Watercress Woods

Head off on an immersive round trip on a vintage steam train, over the hill and into where the witches wait. Inspired by the story of Hansel and Gretel, where families become part of the tale and help protect the train from the Witches of Watercress Woods, the experience promises surprises, character actors and lots of Halloween fun without the fright.

Halloween Witches of Watercress Woods at The Watercress Line. 
Thursday 29 - Saturday 31 October. 
📍Alresford 

Ride on a Halloween Horror Train

Climb onboard a steam train for an adults-only fright night. This Halloween, The Watercress Line welcomes a Séance Train, a moving vessel designed to pierce the veil between worlds. Expect frights, scares and flickering lights as the train sets off on its journey.

Halloween Horror Train (18+) at The Watercress Line. 
Thursday 29 - Saturday 31 October. 
📍Alresford 

Party Halloween-style at the Science Centre

Put on your spookiest costumes for Winchester Science Centre's Halloween silent disco. The centre is open after dark for a family evening of spooky fun, featuring three channels of tunes to choose from while you dance your way around the two floors of interactive exhibits.

Halloween Silent Disco at Winchester Science Centre. 
Saturday 31 October. 
📍Winchester city