September 2026 may be 'back to school' season but that doesn't mean the fun is over. As the first signs of autumn appear, Winchester comes alive with a whole host of cultural events and museum exhibitions that'll cure any end-of-summer blues.
We've got plenty of festivals to keep us busy too, from Heritage Open Days - which opens the door to loads of Winchester's fascinating buildings for free - to Winchester Green Week, a celebration of living sustainably and protecting our planet. Not forgetting all the new openings in Winchester to try this month.
While you're filling your diary with things to do in Winchester this September, why not book a table at one of the city's award-winning dining experiences too, or take advantage of Winchester district's pretty picnic spots and alfresco restaurants while the sun still shines.
Ponder creativity, culture and change at a multi-discipline exhibition
Join Winchester School of Art at their annual MA (Master of Arts) Degree Show to explore all things culture and creativity. See work from a variety of disciplines including Digital Media, Fashion, Fine Art and Curation.
WSA MA Degree show at Winchester Gallery.
Thursday 3 September to Saturday 5 September.
📍Winchester city centre
Enter your pooch into a long-running dog show
Established in 1908, Alresford Show is a one-day celebration of agriculture and rural communities, featuring horse shows, horticultural competitions, vintage farm machinery, a dog show with lots of novelty categories you can enter (dog most like its owner? most adoring eyes?), lots of local food and drink stalls and more.
Alresford Show.
Saturday 5 September.
📍near Alresford
Sing along at a sunset screening
Gather your friends, pack a blanket or pop-up chair, and settle in for a feel-good evening of music, laughter and unforgettable sing-along moments as Mamma Mia fills the outdoor cinema screen. Set against the backdrop of a late summer evening, it’s the perfect opportunity to relax, unwind and enjoy a unique outdoor experience.
Mamma Mia at Voco Hotel.
Friday 4 September.
📍Winchester city
Rave the weekend away on a farm
Get summer festival season fully out of your system with a final hedonistic adventure at Mucky Weekender, a music festival in the countryside just outside Winchester. Goldie 'Live' is the headliner, alongside Dub Pistols and David Rodigan.
Mucky Weekender at Vicarage Farm.
Thursday 10 - Saturday 12 September 2026.
📍near Winchester
Explore amazing buildings for free
Winchester is full of interesting buildings. Pretty ones, ancient ones and ones filled with intriguing treasures to discover. This September, a whole host of them, from The Great Hall and Winchester Cathedral to Winchester City Museum and Winchester College are totally free to enter, thanks to the Heritage Open Days 2026 festival, which sees museums, houses and more open their doors to members of the history-loving public. Please note: some buildings are free to visit for the duration of the festival while others are running free tours or events on selected dates.
Heritage Open Days 2026.
Friday 11 - Sunday 20 September.
📍Various locations across Winchester city and district
Be blown-away by Ballroom dancing
Breaking Ballroom celebrates where ballroom dance has been but also where it can go; and tells a story of glamour, connection, passion, and rebellion. It blends the refined elegance of ballroom dance and classical technique with bold theatrical flair, daring lifts, athleticism, and raw, emotionally-charged movement; tradition with innovation; and precision with risk. By bending the rules of ballroom, the dancers put on an unforgettable performance.
Breaking Ballroom at Theatre Royal Winchester.
Friday 11 September 2026.
📍Winchester city centre
Find your artistic flow
Explore colour, form and personal expressions in a new course and learn ways of expressing atmosphere, memory, emotion and personal experience that words alone often cannot capture. Inspired by artists including Kandinsky, Rothko, Pollock and Picasso, in this five-week course you'll experiment with painting, drawing, mixed media, wire and clay while developing your own individual creative enquiry. There is no right way of working, each participant is encouraged to discover their own authentic visual language.
Making the invisible visible, Quaker Meeting House.
11, 18 & 25 September, 2 & 16 October.
📍Winchester city centre
Eat your way around Taste of Wickham
A celebration of local food, as well as crafts, live music and family fun. The village of Wickham is transformed for the day with over 75 stalls, delicious local food and drink to sample, plus a kid's area where little ones can get stuck into face painting, bubbles and circus skills.
Taste of Wickham.
Sunday 13 September 2026.
📍Wickham
Practise your downward dog in the park
Bring a yoga mat (or a towel) and enjoy a free hour of alfresco Park Yoga in one of Winchester's green spaces. There's no need to book, you just turn up and stretch it out in the great outdoors. A wholesome way to make the most of the end of the summery days.
Park Yoga at Garrison Ground (near Winchester Leisure Centre).
Every Sunday until 13 September.
📍Winchester city
Visit an immersive nature festival
Floral installations will be taking over ancient Winchester Cathedral this month for 'Wild! A Festival of Flowers and Nature'. The festival will see the cathedral bursting with colour and creativity as hundreds of floral designers bring the wild beauty of nature to life through stunning installations, live botanical art, talks and performances. Look out for thought-provoking installations exploring themes of the climate emergency, nature's resilience and our human relationship with the natural world.
Wild! A Festival of Flowers and Nature at Winchester Cathedral.
Tuesday 15 - Saturday 19 September 2026.
📍Winchester city centre
Paint the seasons with Make Space Art
Inspired by the golden glow of sunflower season, this uplifting watercolour experience celebrates the warmth and richness of late Summer. Using fresh sunflowers and seasonal blooms as inspiration, you'll learn how to capture bold shapes, colour and expressive brushwork while enjoying a relaxing morning of creativity.
Fields of Gold at The Chestnut Horse.
Friday 18 September.
📍Easton
Unearth the impacts of the Scottish Colourists
The latest art exhibition to arrive at The Gallery at The Arc, Winchester explores the creation of a new language of colour in European art. The four artists known as the Scottish Colourists: SJ Peploe, JD Fergusson, Leslie Hunter, and FCB Cadell, are acknowledged as one of the most talented, experimental, and distinctive groups in 20th-century British art. This breakthrough touring exhibition sets the radical Scots in the context of their British, Irish, and European contemporaries. Discover the achievements of these great Scottish artists and their peers, and their continuing impact in the story of European art.
Scottish Colourists: Radical Perspectives at The Arc.
Until Wednesday 16 September.
📍Winchester city centre
Join a joyful Jazz festival
Four unforgettable days of world-class live music, vibrant performances, and creative energy. The festival brings together celebrated jazz artists, emerging talent, and exciting family-friendly experiences in a dynamic programme of ticketed and free events - from electrifying big band sounds and groove-driven funk to cutting-edge contemporary jazz, audiences can discover extraordinary music this September.
If you missed the festival, there is plenty of music and jazz in Winchester throughout the year, check out our useful round-up here.
Winchester Jazz Festival 2026.
17-20 September.
📍Winchester city centre
Celebrate all things sustainable
Winchester's annual Green Week is taking place between 19 and 27 September and is made up of a calendar of events run by local communities and environmental groups, as well as green-minded businesses.
Winchester Green Week 2026.
Saturday 19 - Sunday 27 September.
📍Various locations in Winchester city
Chase a PB at Winchester Half Marathon
Starting and finishing outside the Winchester Guildhall, this 13.1 mile route is as scenic as running routes come. Racers will weave past Winchester Cathedral and Winchester College before running along the Water Meadows, catching views of St Catherine's Hill and The Hospital of St Cross. They'll then head out for a stretch in the countryside before returning to the city's pretty centre. There's also a 1km Kids Fun Run at 12:30pm for little legs.
Winchester Half Marathon.
Sunday 20 September.
📍Winchester city centre
Indulge in wine and food on a vineyard tour
Spend a relaxed day exploring Hampshire’s rolling countryside, visiting three outstanding vineyards - Raimes, Candover Brook and Black Chalk. Make the most of a designated driver, guided tours and tastings of sparkling and still wines. Your ticket also includes a two-course lunch!
Vineyards of Hampshire Tour.
Saturday 19 September.
📍Winchester city centre
Shop 'til you drop at a local fair
Browse over 70 quality stalls, with a fantastic range of products including foodstuffs, gifts, homewares, jewellery, beautiful clothes for all ages, useful gadgets, children’s toys and much more. A café will be available all day, serving coffee, cakes and light lunches and Grange wine will be served from a vintage Land Rover Discovery.
Hampshire Fair at the Grange.
Wednesday 23 September.
📍Northington
Reimagine the music of Radiohead
In this unique show, era-defining hits are reimagined through the immersive palette of a full orchestra, faithfully capturing the spirit of a golden era in British music. The rich harmonies and textures of Radiohead’s unique sound world have been sumptuously arranged for strings, harp, woodwind, and percussion, filling a candlelit cathedral with raw emotion and kaleidoscopic colour.
London Concertante at Winchester Cathedral.
Thursday 24 September.
📍Winchester city centre
Experience all things mythical
From battling skeletons and mythical beasts to dinosaurs, dragons and adventures across strange and distant lands, Ray Harryhausen's pioneering stop-motion creations have inspired generations of filmmakers, artists and dreamers. Now, for one special day, that world is being brought to life at The Arc. The day includes classic film screenings, exclusive exhibition tours, a children's creature-making workshop, and a special Q&A with Vanessa Harryhausen.
Hooray for Harryhausen: A Day of Films, Creatures & Curiosity at The Arc.
Saturday 26 September 2026.
📍Winchester city centre
Laugh out loud at a comedy festival
Head to Winchester's Theatre Royal for the Winchester Comedy Festival Autumn Gala, a evening of stand-up comedy from Felicity Ward, Ray Badran, Esther Manito and Tom Deacon (MC).
Winchester Comedy Festival: Autumn Gala 2026 at Theatre Royal Winchester.
Saturday 26 September.
📍Winchester city centre
See out the summer at a Michaelmas Fair
Mark the start of autumn and the shortening of the days with a Saturday spent in the pretty surrounds of The Hospital of St Cross. The annual Michaelmas Fair will feature live music, a wide range of artisan makers, craft stalls and local producers, traditional calligraphy workshops, classic cars and open-air games and entertainment throughout the day.
Michaelmas Fair at The Hospital of St Cross
Saturday 26 September.
📍Winchester city
More September events
Garden Tour
Jane Austen's House
DATE: 18 Sept 2026 - 18 Sept 2026
Jane Austen Study Afternoon
Jane Austen's House
DATE: 18 Sept 2026 - 18 Sept 2026
Nature Writing Workshop
Jane Austen's House
DATE: 20 Sept 2026 - 20 Sept 2026
The Three Musketeers
Royal Armouries: Fort Nelson
DATE: 4 Sept 2026 - 4 Sept 2026
Vox Lumiere Metropolis
Theatre Royal Winchester
DATE: 18 Sept 2026 - 18 Sept 2026
Marvin Muoneké's Big Band
Theatre Royal Winchester
DATE: 19 Sept 2026 - 19 Sept 2026
Ministry of Science: Science Saved the World
Theatre Royal Winchester
DATE: 13 Sept 2026 - 13 Sept 2026
Life drawing with Terry
Winchester Royal Hotel
DATE: 20 Sept 2026 - 20 Sept 2026
Wargaming in the British Army - an evening talk
The Royal Logistic Corps Museum
DATE: 24 Sept 2026 - 24 Sept 2026
Summer of Play at The Vyne
The Vyne
DATE: 23 Jul 2026 - 13 Sept 2026
Mamma Mia! Sunset Screening
voco Winchester Hotel & Spa
DATE: 4 Sept 2026 - 4 Sept 2026
Macbeth
Theatre Royal Winchester
DATE: 16 Sept 2026 - 17 Sept 2026
Bangers and Mash Train - Watercress Line
The Watercress Line
DATE: 17 Sept 2026 - 17 Sept 2026
Andy Hamilton's Night To Remember
Theatre Royal Winchester
DATE: 20 Sept 2026 - 20 Sept 2026
Michael Spicer: Hope all's well
Theatre Royal Winchester
DATE: 24 Sept 2026 - 24 Sept 2026
Scott Bennett: Stuff
Theatre Royal Winchester
DATE: 23 Sept 2026 - 23 Sept 2026
A Tribute to Sting and The Police
Theatre Royal Winchester
DATE: 12 Sept 2026 - 12 Sept 2026