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 3:00pm, when the fair opens.

Image: E J Westmacott

Michaelmas Fun Fair in Alresford. Thursday 16 October.

Complete the Spooky Winch word hunt

There are loads of things to do in Winchester for Halloween and October half-term. One of them is this totally-free word hunt which will take you and your little one around the city looking for spooky signs in shop windows. Pick up a trail sheet from the Visitor Information Centre, The Arc or Winchester City Museum - then return the finished sheet to receive a Halloween treat.

Spooky Winch Word Hunt, Winchester City Centre. From Saturday 18 October.

Meet Winchester's new Jane Austen statue

Jane Austen fans already travel to Winchester to see her grave in Winchester Cathedral and No. 8 College Street, the house in which the author died, as well as Jane Austen's House in nearby Chawton. As of October 2025, there will be another reason: a statue of Jane Austen in the city centre. The outdoor memorial, by sculptor Martin Jennings, will stand in the Cathedral's Inner Close from 16 October. Set against the backdrop of No 9 the Close, she will stand as an authoritative and elegant figure, with her characteristic ringlets and cap, by her famous writing table. The statue will be unveiled following a Jane Austen Anniversary Service at the Cathedral. This is free for the public to attend but will be ticketed. Find more things to do to mark 250 years of Jane Austen here.

Unveiling of the Jane Austen Statue, Winchester Cathedral's Inner Close. Thursday 16 October.

Celebrate Oktoberfest at Dummer Down Brewery

If you're swerving Sober October this year, head to Dummer Down Brewery on 4 October for a Bavarian-style celebration. Expect live music, games and singalongs from Von Hit Vonder Bunde, as well as food trucks, a fire pit and a lot of local beer. Book tickets in advance - this one sold out last year.

Oktoberfest at Dummer Down Brewery. Saturday 4 October.

Watch a play about intergalactic star-crossed lovers

Families will love this joyful show, based on the book by Julia Donaldson and Axel Scheffler. It's Romeo and Juliet meets outer space, following a sweet alien couple whose families disapprove of their love. Expect rocket ships, strange planets and grumpy alien grannies.

The Smeds and the Smoos at Theatre Royal Winchester. Friday 3 October - Sunday 5 October.

Learn how to cook like a winner

Up your culinary game with a masterclass at Lainston House's Season Cookery School. This month their resident chef Tom Hamblet, who won MasterChef: The Professionals, is teaming up with Great British Bake Off winner Matty Edgell to teach participants how to ace a two-course dinner worthy of guaranteeing first place.

Masterclass: Matty Edgell & Tom Hamblet at Lainston House, Winchester. Friday 10 and 24 October.

Immerse yourself in the world of heritage steam trains

Vintage train fans will want to hotfoot it to The Watercress Line this month. Over the first weekend in October, the heritage railway is celebrating all things steam. There will be unlimited rides on the line's locomotives as well as rides on visiting locomotives. Book in advance for guided tours of the Engineering Works, driving experiences and brake van rides.

Autumn Steam Gala at The Watercress Line, Alresford. Friday 3 to Sunday 5 October.

Catch Beyond the Bonnets before it closes

The Arc's current exhibition gives a voice to those who were overlooked by many but not neglected in Austen’s novels: working women. It's a compelling, heartwarming and emotive look at the unexpected and often precarious lives of working women at the time - and it's only on until 2 November, so go this month if you don't want to miss out.

Beyond the Bonnets: Working Women in Jane Austen's Novels at The Arc, Winchester. Until 2 November.

Laugh at Jenny Eclair's jokes (jokes jokes)

Comedian Jenny Eclair is at Winchester's Theatre Royal this month, performing her autobiographical show which takes fans from drama school tales to becoming a nana, via cider, bedsits and punk poetry.

Jenny Eclair: Jokes Jokes Jokes Live! at Theatre Royal Winchester. Saturday 4 October.

Go to a séance at Winchester Poetry Festival

There are a whole host of events, talks and workshops to attend as part of Winchester Poetry Festival 2025. One of which is a performative séance celebrating 10 years of Dead [Women] Poets Society. Poets Joelle Taylor and Mary Jean Chan will commune with the spirits of two legendary writers who have influenced their work. Other festival events include a reading from Robin Ince at P&G Wells bookshop, an Arthurian workshop and a poetry collage session for all-ages. Most events take place between 10 and 12 October at The Arc.

Winchester Poetry Festival, The Arc and various locations. 2 - 12 October.

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 11 October. There will also be a witchy Halloween half-term trail through the gardens between Saturday 18 October and Sunday 2 November.

Image: ©National Trust Images/Sophie Bolesworth

Hinton Ampner, near Winchester. From Saturday 11 October.

Spend a chilled Sunday at a sound bath

Experience a deeply restorative hour in New Energy Yoga's cosy studio immersed in the soothing sounds of Himalayan and crystal bowls and gongs. During this Sound Bath Immersion, sound therapist Michelle Dennison-Hall will combine different sounds to create a relaxing and therapeutic effect. A chilled way to round off a weekend in Winchester.

Sunday Sound Bath Immersion at New Energy Yoga, Winchester. Sunday 19 October.

Have a go at calligraphy with the Winchester Cathedral scribes

The Scribes Open Day at Winchester Cathedral is a free and unique opportunity to witness the ancient art of calligraphy in action. Watch the Cathedral Scribes (the only group of its kind based in any English cathedral) as they demonstrate their incredible skills, bringing words to life with beauty and precision. Visitors of all ages are also invited to try their hand at calligraphy and create a piece of history for themselves. This event is family-friendly, with creative activities that little ones can enjoy too.

Scribes Open Day at Winchester Cathedral. Saturday 11 October.

Play a camp and chaotic game of bingo

Head to The Nutshell to join award-winning character comedian Tracey Collins as she hosts Bingo at Tiffany’s with Audrey Heartburn. Enjoy an evening of hilarious bingo games, ridiculous live songs, dancing, prizes and joy!

Bingo at Tiffany's with Audrey Heartburn! at The Nutshell, Winchester. Saturday 11 October.

Read a handwritten Austen poem

Take the opportunity to visit the original manuscript of Jane Austen’s poem, in her hand, about the death of her close friend, Mrs Anne Lefroy. It's on display as part of the Kings & Scribes exhibition at Winchester Cathedral until 19 October, when it will return to the archives.

Angelic Women: The Friendship of Jane Austen and Anne Lefroy at Winchester Cathedral. Until 22 September.

Graduate from Broomstick Academy

Droxford Pumpkin Patch returns for 2025 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, near Bishop's Waltham. Friday 24 October - Saturday 1 November.

Dance at a grown-up disco

Discos for Grown Ups is taking over beautiful Bapsy Hall at Winchester's Guildhall for a night of 70s disco, 80s pop and 90s dance classics. There will be retro sweets, people in disco finery and the likes of Donna Summer, Chaka Khan, Abba and Faithless to dance away to.

Discos for Grown Ups at The Guildhall, Winchester. Saturday 18 October.

Grab a seat on the Wizard Express

The Watercress Line is transformed for October half-term into a magical world of wizards, witches and spooky fun. Ticketholders can ride on the Wizard Express, make slime, learn circus skills and take part in the daily fancy dress competition.

Wizard Week at The Watercress Line, Alresford. Saturday 25 October - Sunday 2 November (not running on 27 October).

Watch Jaws in a gin distillery

Visit the Bombay Sapphire gin distillery, which is outside of Winchester, after dark to watch a screening of classic thriller Jaws in the on-site Sapphire Cinema. Your ticket price includes a gin and tonic cocktail from the Turbine Bar on arrival as well as popcorn and sweets for munching during the film.

Jaws: Cinema Nights at Bombay Sapphire Distillery, near Winchester. Sunday 26 October.

Brace yourself for a fright at Spookesbury

Ramp up the scares this Halloween with a trip to Spookesbury. By day it's all family-friendly pumpkin decorating and trips through the hay bale maze. By night it's designed to make you jump, with Scare Nights featuring terrifying walk-through attractions as well as roaming actors intent on frightening guests. There's also food trucks, a Day of the Dead bar and DJs.

Spookesbury: Harvest and Haunt, near Wickham. Wednesday 29 October - Sunday 2 November.

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. Elsewhere in Winchester district, The Woolpack Inn is a cosy countryside pub near Alresford that has recently reopened after a refurbishment.

Get the Regency gossip on a guided tour

Let yourself be transported to Jane Austen’s Winchester, in celebration of the author’s 250th birthday, on this guided walking tour. The 90-minute wander will be led by one of Winchester’s professional guides and lots of scandalous stories are guaranteed.

In Flagrante Delicto: Regency Scandals Guided Walking Tour, at Winchester Visitor Information Centre. Saturday 18 October.

Party with pumpkins and glowing face paint

Put on your spookiest costumes for Winchester Science Centre's UV Halloween Pumpkin Party. The centre is open after dark for a family evening of UV fun, featuring a live DJ, glowing face painting, unlimited squash, and a sweet treat to take home. You and your little ones will also get to explore two floors of interactive exhibits.

Halloween UV Pumpkin Party at Winchester Science Centre. Wednesday 29 October.

See a much-loved Gilbert and Sullivan opera

Charles Court Opera are bringing their critically-acclaimed, 5-star production of The Mikado to Winchester. The Mikado is one of the most loved of Gilbert and Sullivan's operas and this cast will be made up of some of the UK's finest young singers.

The Mikado at Theatre Royal Winchester.  Thursday 16 and Friday 17 October.

Set off on a flavour-led foraging walk

The Grange, near Alresford, is the starting point for a walk with a foraging expert Flavour Fred. (An exact location is shared once you've secured your spot.) The two-and-a-half-hour wander will be an introduction to foraging, identification and the risks of wild food and drink, as well as preservation and preparation. Expect a few tasters along the way.

Flavour-Led Walk with Flavour Fred, near Alresford. Saturday 18 October.

Watch a horror film - with cake and cocktails

Get your sugar fix and your thrills at the same time at Cabinet Rooms. The cosy café bar has a secret screening room downstairs with room for 10 cinemagoers. This October they are running multiple screenings of the 2024 remake of Nosferatu. You get a complimentary drink with your ticket - or you could upgrade to a Cake & Cocktails Club ticket to get a welcome drink, plus a cake and a cocktail to enjoy during the movie.

Nosferatu at Cabinet Rooms, Winchester. Multiple dates in October.

Try a sociable yoga class

If you like your workouts with a side of socialising and swiftly followed by pizza try one of the Yoga Social Club Winchester's classes. In October, they're hosting Pranayama and Pizza, a yoga class followed by pizza and prosecco at new Winchester restaurant Olivetta. The code VISITWINCH10 will get you 10% off any booking made before 31 October.

Pranayama and Pizza with Yoga Social Club Winchester. Wednesday 29 October.

Sip local pints on the Real Ale Train

Sample pints from local Hampshire breweries, poured in the bar car while you travelling by train through the countryside. The Real Ale Train experience lasts around three and a half hours. There's also food served on board and you get a free pint if you book in advance online. Oktoberfest and Halloween fancy dress are encouraged for the October dates!

Real Ale Train at The Watercress Line, Alresford. Saturday 11 and Saturday 25 October.

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’. You could also try a section of The South Downs Way, pick up the Meon Valley Trail which runs from West Meon to Wickham or wander The Millennium and Alre Valley Trail which takes in the pretty countryside around Alresford. 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.