Make mega school summer holiday memories

School's out for summer 2026, and that means you've got some serious planning to do. Luckily, Winchester is full of exciting and entertaining things to do for kids and their grown-ups over the school summer break. There's easily enough to fill six weeks of fun, which is a good job really. In Hampshire, the school summer holidays officially run from Thursday 23 July until Monday 31 August 2026, but you can probably expect an inset day or two tagged on the end too. From silent discos and museum sleepovers, to flower-crown workshops and pirate-themed play trails, keep reading to discover events and things to do with your kids, from toddlers to teens, over the school summer holidays in Winchester.

Read: School summer holidays in Winchester: 28 fun things to do

Tour Winchester's local vineyards - with a designated driver

Spend a relaxed day exploring Hampshire’s rolling countryside, visiting three outstanding vineyards and tasting award-winning English wines - all hosted by an expert guide. Grape & Grain Tours will be your designated driver, taking you to visit Raimes, Candover Brook and Black Chalk, where you’ll enjoy guided tours and tastings of sparkling and still wines. Your ticket includes a two-course lunch at The Tichborne Arms pub near Alresford.

Vineyards of Hampshire Tour, departing from Winchester Train Station. 
Saturday 1 August. 
📍Winchester city centre 

Read more: Dreamy vineyards to visit near Winchester

Play a medieval escape game in a genuine medieval setting

Step back to 1445 in a thrilling race against time! You have just 60 minutes to uncover hidden treasure in an immersive escape game set within the stunning medieval buildings of The Hospital of St Cross. Your investigation will take you through rarely seen areas of this historic site, culminating in an escape room challenge deep within its ancient underbelly.

The Crusader's Collectible at The Hospital of St Cross.
Sunday 2, Sunday 9, Sunday 16, Saturday 22, Sunday 23, Saturday 29, Sunday 30 and Monday 31 August. 
📍Winchester city 

Laugh out loud at Winchester's newest comedy club

Helch Market, the city's new food hall, has launched a weekly comedy night. Expect a mix of award-winning comedians and rising stars over two hours of laughs every Sunday night. Tickets are £12.

Helch Comedy Club at Helch Market. 
Sunday 2, 9, 16, 23, 30 August. 
📍Winchester city centre

Explore a new play area inspired by chalk streams and ecosystems

Winchester Science Centre has just opened Play Wild!, a new outdoor play space made up of three areas inspired by the remarkable chalk landscape that shapes Winchester's local environment. Little ones will be able to dig for fossils and climb across a giant mosasaur skeleton to uncover the secrets of the prehistoric chalk sea at Dino Dig, before wading into the wonders of The Chalk Stream, experimenting with water flow and discovering the creatures that depend on this rare and unique habitat. Then they'll climb, crawl and explore Dormouse Den, uncovering the hidden world of one of our most elusive woodland mammals and the delicate ecosystem it calls home.

Play Wild! at Winchester Science Centre. 
Open now. 
📍Winchester city

Mark the changing of the seasons on a nature walk

Join a small group of others to mark Lammas, a turning point in the year and the first of the harvest festivals. The guided 90-minute walk, setting off from the bottom of St Catherine's Hill, will invite you to look for the subtle shifts taking place in the natural world around you.

Lammas Walk at St Catherine's Hill. 
Tuesday 4 August. 
📍Winchester city 

Ride the rails on Thomas the Tank Engine

Hop on board a train ride with Thomas, a real steam engine, watch the exciting live shows with Sodor Station Sweepers Rusty & Dusty, join in the Thomas & Friends character hunt, have fun with the garden games and keep the beat going at the Music Corner packed with music-inspired fun, plus more summer holiday fun.

Day Out With Thomas at The Watercress Line. 
Tuesday 4 - Sunday 9 August. 
📍Alresford

Catch a sunset movie screening

Kick back with a blanket in the pretty grounds of Lainston House for a screening of a classic movie as the sun goes down. You can bring your own picnic to enjoy or upgrade your movie ticket to include wood-fired pizza and brownies too. Films range from Bridesmaids and Breakfast Club to Mamma Mia and Thelma and Louise.

Outdoor Cinema Nights at Lainston House.
Thursday 6, Saturday 8, Thursday 13, Friday 14, Saturday 15, Thursday 20, Saturday 22, Thursday 27, Friday 28 and Saturday 29 August. 
📍near Winchester city

Enjoy Friday night aperitivo at a gin distillery

Ease into the weekend with a relaxed Friday evening at Bombay Sapphire Distillery. Their new Aperitivo Evenings include a fun speed cocktail masterclass, the opportunity to explore the distillery and its glasshouses, and a Bombay Sapphire Sparkling Lemon Cocktail in the Mill Bar terrace overlooking the River Test. From there you can continue your evening with more cocktails and seasonal small plates, if you wish.

Aperitivo Evenings at Bombay Sapphire Distillery. 
Friday 7, 14, 21 and 28 August. 
📍near Whitchurch 

Watch the solar eclipse in Winchester

Catch the UK’s best solar eclipse of the century at Winchester Science Centre. Share a peak viewing moment, guided by experts and with a pair of eclipse viewing glasses included in every ticket. You'll also be able to dive into the science behind the spectacle. Take part in hands-on activities, explore how eclipses happen and watch a planetarium show about eclipses. There will also be face painting, music and crafts.

Solar Eclipse: Live at the Science Centre. 
Wednesday 12 August. 
📍Winchester city 

Don't fancy heading to Winchester Science Centre? You'll be able to see the solar eclipse in Winchester from any high point with a clear view of the western horizon. The partial eclipse will begin at 6:18pm, ending at 8:07pm and peaking at 7:14pm. Fingers crossed for no cloud cover!

Go to an elephant rave at the zoo

The party is on at Marwell Zoo over the school summer holidays - and it’s going to be wild! Boogie on down to DJ Froggie’s silent disco, join the Elephant Rave to help the visiting elephant learn some dance moves, and enjoy lawn games and crafts all over the zoo. There will also be glitter tattoos for tiny festival-goers.

Zoofest at Marwell Zoo.
Until Monday 31 August. 
📍near Winchester city 

Head off on an architecture-themed bike ride

Join RIBA Hampshire for an architectural tour exploring some of Winchester’s bespoke houses. The excellent cycle ride route focusses on local homes. The group will set off at a relaxed pace, stopping along the way to explore key buildings and the stories behind their architecture, before wrapping up at The Willow Tree pub for well-deserved refreshments.

RIBA Hampshire Cycle Ride, from The Willow Tree pub. 
Wednesday 12 August. 
📍Winchester city centre 

Lose yourself at Boomtown festival

August in Winchester means the arrival of Boomtown festival and this year is set to be the most 'unpredictable' and 'diverse' Boomtown yet. Expect surprising acts, a wide spectrum of musical genres and "themed districts bursting with unique design, ground-breaking stages, vivid characters, and unforgettable experiences." The festival organisers describe this year's festival as not "just a festival - it’s a holiday to a parallel world." The line-up for 2026 includes Scissor Sisters, Skrillex and Shaggy.

Boomtown 2026.
Wednesday 12 - Sunday 16 August. 
📍near Winchester city

Sleep overnight at the Science Centre

Bring your own sleeping bag and pillow for an overnighter at Winchester Science Centre. Your ticket gets you evening access to the exhibition floors, a live science show, a guided tour of the Lunar Experience, a live Planetarium show and the chance to set up camp and snooze somewhere incredible. You also get breakfast the following morning to finish the adventure.

The Big Family Sleepover at Winchester Science Centre.  
Saturday 15 - Sunday 16 August. 
📍Winchester city

Contribute to a giant music-inspired painting

Explore how sound, rhythm and imagination come together, using music as the starting point for making something bold and expressive. In this lively, collaborative session, children can create one long, colourful artwork together. As the music plays, kids will respond to the beats, rhythms and sounds through paint, marks and movement. Expect a relaxed, slightly messy and very joyful atmosphere, with music ranging from calm to loud and playful to keep things interesting.

Summer Holidays: Let's paint to music! at The Arc.
Tuesday 18 August. 
📍Winchester city centre

Listen to jazz in Winchester Cathedral grounds

Unwind at dusk and discover a hidden haven in the city centre for a new series of open-air Jazz Lates in the Winchester Cathedral Café Garden. Jazz Lates offers a relaxed, family-friendly evening in a section of the Cathedral grounds that hasn’t been open to the public in the evening before. Enjoy live jazz music, freshly cooked pizza from the outdoor oven, Jude’s ice-cream, and Chalkdown sparkling wine.

Jazz Lates at Winchester Cathedral Café Garden.
Thursday 20 August. 
📍Winchester city centre 

Go on pirate and Pokémon-themed family fun trails

Head to a local National Trust property this month to get stuck into their Summer of Play. The Vyne has dressing up, sack races and balance beams (Thursday 23 July - Sunday 6 September), while Hinton Ampner has pirate-themed activities to try (Saturday 18 July - Sunday 6 September) and Mottisfont is calling all Pokémon fans new and old to join in their Summer of Play (Thursday 23 July - Sunday 6 September).

Summer of Play at National Trust properties. 
📍various locations 

Rave after dark in the park

The Ibiza Orchestra Experience is descending on River Park in Winchester for a night of classic dance tunes performed by a 26-peice band. As well as the main stage, you'll find a Disco Tent and a silent disco area, plus live support acts and DJs.

The Ibiza Orchestra Experience at River Park. 
Friday 21 August. 
📍Winchester city centre 

Learn about medieval sword fighting

Basingstoke HEMA (Historic European Martial Arts) and Andover HEMA will be displaying their skills with clashes of swords and armour in the magnificent, historic setting of The Great Hall. Sword fighting experts will be battling it out with demonstrations and talks over the course of the day.

Medieval Sword Fighting at The Great Hall. 
Saturday 22 August. 
📍Winchester city centre 

Eat and drink your way around a sausage and cider festival

Join Sausage and Cider Festival for a spectacular day of festival fun including 30+ cider flavours and more than 20 sausage flavours. There will also be live performances and DJ sets from Bay City Rollers, Barrioke, Pat Sharp, Matthew Horne (of Gavin and Stacey fame), pus activities like axe throwing, circus skills, a silent disco and more.

Sausage and Cider Festival at River Park. 
Saturday 22 August. 
📍Winchester city centre 

Sample local ales in the sun

Okay, so August bank holiday sunshine isn't exactly guaranteed, but you're bound to have a good time whatever the weather at the annual Flower Pots Beer Festival. The pretty Cheriton pub, which brews its own outstanding pints, will be the setting for more than 20 live music acts, as well as 20 traditional cask ales and over 100 guest ales and lagers from independent UK breweries. Children and dogs are welcome.

The Flower Pots Beer Festival at The Flower Pots Inn & Brewery. 
Friday 28 - Sunday 30 August. 
📍Cheriton  

Listen to live music in a South Downs meadow

The Alton Concert Band will be performing live outside in the meadow at Gilbert White’s House. They'll perform a crowd-pleasing programme featuring Proms favourites such as Jerusalem and Pomp and Circumstance, alongside hits from The Greatest Showman, ABBA on Broadway and The Lion King. Bring a picnic blanket or low-backed chair and enjoy great music in a beautiful setting.

Proms: A Magical Evening of Music at Gilbert White's House. 
Friday 28 August. 
📍Selbourne, near Alton 

Pick your own giant sunflowers

Soak up the sunny sight of 10-acres full of bobbing yellow sunflowers this August. At Silkstead Sunflowers just outside Winchester, you'll find a sunflower maze and viewing tower, a family-friendly trail with cute photo opportunities and a picnic area with games for little ones. Entry fee also includes three sunflower stems to pick and take home. Visit on Sunday 30 August for the Silkstead Sunflowers Summer Sundowner, an end-of-season celebration with added fun.

Silkstead Sunflowers at Four Dells Farm.
Opening August, date TBC. 
📍near Otterbourne