Ride around the quiet city on vintage buses - for free

Kick off 2026 with a purse-friendly, wholesome New Year's Day activity. Friends of King Alfred Buses will be running free rides around Winchester city and its surroundings on their magnificent heritage buses. Departing from the Broadway in Winchester city centre, the free rides will take you along Winchester's main roads, when the usual buses aren't in service.

Friends of King Alfred Buses on New Year's Day, Winchester. Thursday 1 January.

Dance at an alcohol-free rave

Doing dry January, or just want something a bit different from your nights out? Loud & Clear is an underground dance music party Winchester that intends to be inclusive, safe, alcohol-free, drug-free, and fully focused on the music. Discover DJs, dance music and deep bass - it's an uplifting rave experience with a friendly, welcoming crowd.

Loud & Clear at Unit 12, Winchester. Saturday 3 January.

Discover hidden treasures at Winchester College

See Winchester College’s collections, including highlights from the art collections and rare books, which are not normally on public display. Led by the Museum and Collections Manager, visitors will explore the College’s art gallery and original museum, ‘Musa’, where oil paintings, watercolours, and tapestries are on show. You will also visit part of the Fellows’ Library, where there is a changing display of rare books and manuscripts, prints, and drawings.

Winchester College Treasures Tour. Monday 5 January.

Watch a West End play recorded live

See Jack Lowden and Martin Freeman in the West End production of The Fifth Step. The stage show has been filmed live from London's Soho Place, and is now showing at selected theatres and cinemas. The play tells the story of James, who becomes a sponsor to newcomer Luka, after years in the 12-step programme of Alcoholics Anonymous. "The pair bond over black coffee, trade stories and build a fragile friendship out of their shared experiences. But as Luka approaches step five – the moment of confession – dangerous truths emerge"...

National Theatre Live: The Fifth Step at Theatre Royal Winchester. Thursday 8 January.

Eat your way through Winchester's best vegan dishes

Whether you're kicking off your year by embracing Veganuary, or already love all things plant-based, there's no better time to try out some of Winchester's hottest veggie and vegan offerings. Open House Deli is a great place to head. Their menu is a mix of veggie and vegan, with brunch options, mega salads and delicious plant-based cakes on the counter. Elsewhere, there are so many brilliant bites to try in Winchester, from Overdraft's vegan grilled nopales tacos to Lucky Lychee's marmite tofu and the mushroom and leek sourdough toastie at Cabinet Rooms.

Image: Lucky Lychee 

Read: Vegetarian and vegan Winchester 

Sing to the apple trees

Head to Chawton House to join a centuries’ old Twelfth Night apple-growing celebration, where participants will sing in the orchard to encourage a plentiful harvest in 2026. There will be soup, cider and hot drinks in the Courtyard before a procession led by the Wassail Queen through the grounds of Chawton House to the orchard, where bad spirits will be warded off by a tree blessing. You're encouraged to bring along an instrument (or anything that will help make a noise!) The Kings Pond Shantymen will also perform traditional songs.

Evening Orchard Wassail. Chawton House, Chawton. Saturday 10 January.

Take a William Morris watercolour workshop

Improve your painting skills at a day-long watercolour workshop. Run by professional artist Nicky Bell, the workshop will look into the style of William Morris, who is the subject of The Arc's current art exhibition. Throughout the day, participants will consider the core elements that make up Morris' much-loved patterns, create their own designs and develop their painting style.

Nature's Timeless Patterns: A William Morris Watercolour Workshop at The Arc, Winchester. Saturday 10 and Saturday 17 January.

Hike a half-marathon

Kick off 2026 with a bracing stomp around Winchester's stunning countryside. The Winchester Hiking Trail is an off-road hiking challenge, following picturesque tracks, bridleways, and footpaths around Farley Mount. It's open to walkers of all abilities; you can choose to hike a half marathon (21k) or take part in a 12k walking challenge. Sign up to take part in the organised hike and you'll have one accomplishment under your belt just 11 days into the new year!

Winchester Hiking Trail. Sunday 11 January.

Go to a French cinema night

Is 2026 going to be the year you finally learn French? A ticket to this French film night includes a welcome drink, a French sweet treat and the opportunity to stay for a post-film discussion at the end of the screening. The film under the spotlight will be 2022 comedy Pétaouchnok, screened in French with English subtitles, so the event is accessible to both French speakers and newcomers to French cinema.

La France fait son Cinema: Pétaouchnok at The Arc, Winchester. Tuesday 13 January.

Do a deep drive into the history of the Kray twins

Broadcaster Fred Dinenage presents an evening of expert insight on twins Ronnie and Reggie Kray as the official biographer to Britain’s most notorious gangsters. The TV presenter and author, who was chosen by the brothers to tell their official story and given unparalleled access to their lives, shares fascinating tales about the twins and his experience of sending time with them.

Ronnie, Reggie and Me with Fred Dinenage at Theatre Royal Winchester. Thursday 15 January.

Start 2026 free of stress

Join this workshop which promises a powerful journey through body and mind to release habitual stress patterns. The 150-minute class will involve somatic movement, breathwork and fascia release as well as hypnosis and sound healing, with crystal bowls and gongs. The outcome? "A total re-charge of body, mind and spirit and... a calmer, clearer more centred and peaceful version of you."

Hypno-Somatics: Releasing Stress at the Root at New Energy Yoga, Winchester. Saturday 17 January.

Check out some really old bikes

Join the Veteran Cycle Club outside the front of Winchester City Museum to celebrate the birthday of Dickie Frost, a Winchester resident and champion cyclist of the 1890s. Discover historic bicycles from the Victorian period through to the late 1930s on display in the Square. Veteran Cycle Club members will also be on hand to demonstrate how these historic bicycles were ridden, maintained, and raced.

Vintage Bicycle Display: Veteran Cycle Club, outside Winchester City Museum. Sunday 18 January.

Go on a big mums' night out

Get a babysitter for an evening with the Scummy Mummies. (They're a comedy double act with an award-winning podcast and live comedy show FYI) From menopause to mansplaining, teenagers to Tinder, no subject is safe. You can expect brand new songs, sketches, stand-up, and plenty of sparkly catsuits.

Scummy Mummies: Hot Mess at Theatre Royal Winchester. Wednesday 21 and Thursday 22 January.

Step inside a Van Gogh masterpiece

Van Gogh Alive, the most visited multisensory experience in the world, is coming to Winchester in 2026. The event sees the artist's masterpieces come to life, giving you the sensation of stepping within his paintings. At Winchester Science Centre, Van Gogh Alive will take over the planetarium dome where you will be transported through Van Gogh’s world, from the Netherlands to Arles, surrounded by over 3,000 stunning images of his most famous works, including 'Starry Night' and 'Sunflowers' - and it'll all be set to a powerful classical score.

Van Gogh Alive at Winchester Science Centre. Thursday 22 January - Sunday 22 March.

Find out if folk songs and stand up can save the world

Protest songs and folk music meet stand up comedy in Grace Petrie's new show, which is coming to The Arc in Winchester this January. Petrie is set to combine music and comedy for the first time, for a show which tackles fascism, misogyny and the climate crisis. "She knows folk songs can't save the world, and neither can stand up. But both at the same time?" Let's find out.

Grace Petrie: This is no time to panic! at The Arc, Winchester. Friday 23 January.

Try out being part of Winchester Cathedral choir

Have you ever wondered what it’s like to be part of a world-class choir? Girls in years 5, 6 and 7 are invited to come and experience the life of a chorister at Winchester Cathedral this month. Girls can join in singing workshops, explore the cathedral, and get a taste of the unique musical training that comes with being part of the prestigious choir. They’ll even have the chance to sing with current choristers and learn what it takes to be part of this amazing tradition. This event is free but booking is essential.

Be a Girl Chorister at Winchester Cathedral. Saturday 24 January.

Celebrate Burns Night with a Nepalese twist

Gurkhas have a long history and affiliation with Scotland and Scottish Regiments. Celebrate this relationship, as well as the poet Robert Burns, with a Burns Night party in The Gurkha Museum in Winchester. Guests will get an arrival drink and the chance to tour the Museum before dinner is served in the McDonald Gallery. Expect a three course Scottish themed dinner, with a Nepalese twist. Tartan is optional but encouraged!

Burns Night at The Gurkha Museum, Winchester. Saturday 24 January.

Discover the female writers Jane Austen loved

Just because Jane Austen's 250th anniversary year is over doesn't mean our love affair with Austen is. During January 2026, Jane Austen's House in nearby Chawton is celebrating all things Pride and Prejudice with a series of tours, talks, readings and performances. Check out Rebel Readings, a session where actors will showcase the female writers Austen herself loved and was inspired by. There's also a new exhibition about Pride and Prejudice being performed on the stage that you can check out while you're there.

Pride and Prejudice Festival at Jane Austen's House. Saturday 24 - Wednesday 28 January.

Get up close to the Sun

There's no need to dream of warmer climes this winter when Winchester Cathedral is welcoming the Sun itself. 'Helios', an artwork by Luke Jerram, will be suspended inside the ancient cathedral from the end of January until the beginning of March, filling the space with a warm glow. You'll be able to get up close with the orb, which features detailed imagery of the Sun’s surface, with standard entry or you can let the sight brighten up your new year at an event. Pilates classes, folk gigs, silent discos and talks are all taking place in the sunshine. Who needs vitamin D supplements?

Here comes the Sun at Winchester Cathedral. Friday 30 January.

Learn about Japanese artists' books

Visit The Winchester Gallery between January and March to ponder what a book is and what it can be. 'Folding Space' is the gallery's newest exhibition bringing together contemporary book artworks and artists’ books made in the UK and Japan. This exhibition is part of a wider series of projects that explores the connection between UK and Japanese artists and the books they make.

Folding Space at The Winchester Gallery. 30 January - 28 March.

Twirl and whirl at a magical family performance

Inspired by Sufi mystic Rumi, this show at The Nutshell in Winchester is a magical and interactive performance for children aged 2-7 and their families. You'll follow three wanderers as they search for belonging in places, with people, or in a feeling. Ticketholders are encouraged to twirl, whirl and play as performers take you on a spellbinding journey to find a place to call home. This non-verbal, sensory show is a charming introduction to dance theatre for little ones.

EVIM [my home] at The Nutshell. Saturday 31 January.

Warm up after a wintery walk in Winchester

Set off on a wintery walk around Winchester's frosty countryside before ending up in a cosy pub. Ideally beside a roaring fire. Even better if you've also ordered a hearty Sunday roast with buckets of gravy on the side. It's the perfect way to spend a chilly, grey weekend in Winchester district. You could do a stomp up St Catherine's Hill (pictured) for views of Winchester city before winding your way back down for lunch at the Wykeham Arms. Or perhaps take in Alresford's Millennium Trail which passes conveniently by lots of great roast lunch options, like The Globe, The Town House and The Swan Hotel.

Read: Sunday roasts in Winchester