THEATRE

Chaos, mischief and plenty of laughs as The Cat in the Hat springs onto the stage at Basingstoke’s The Haymarket this 2–3 May. A lively 45-minute show perfect for little ones, the iconic troublemaker turns a dull, rainy day into a whirlwind of tricks, mayhem and madcap adventure.

Meanwhile in Southampton, Zog takes to the stage at Mayflower Studios (14–17 May) in this colourful musical based on the Julia Donaldson classic following the accident-prone dragon on his quest to win a golden star – with a little help from a kind-hearted girl with medical ambitions.

A powerful, heart-on-sleeve musical experience for teens and adult audiences, local production company CCADS Theatre presents Dear Evan Hansen at The Kings Theatre Portsmouth (7–9 May), the moving story of a socially anxious teen, exploring identity, mental health and connection.

And along the coast, rock ’n’ roll nostalgia hits Southampton’s Mayflower Theatre (21–23 May) as feel-good West End hit, The Buddy Holly Story celebrates the life and music of the legendary musician, from Texas beginnings to global stardom, with iconic hits like That’ll Be The Day and Oh Boy.

FITNESS & OUTDOORS

Enjoy a good ramble? Best foot forward for the Isle of Wight Walking Festival (9–17 May), a feel-good celebration of the great outdoors. With routes for all abilities – from gentle strolls to full-day hikes – it’s a great way to explore the Island’s stunning scenery and wildlife.

And officially under starters orders, the ABP Southampton Marathon, a full marathon, half, 10k or 5k event on 3 May winds past iconic city sights. If you’re not taking part, cheer on the rest and don’t miss the special Supermarine Spitfire start-line fly past, marking the aviation icon’s 90th anniversary in 2026.

FESTIVALS, FAIRS & SHOWS

BBC Gardeners’ World Spring Fair at Beaulieu in the New Forest on Friday 1 – Sunday 3 May 2026. — Image: BBC Gardeners’ World Spring Fair

Whatever you love, there’s plenty to fill the diary this May. Kick off the month with gardening glory, food and fun in the New Forest at the BBC Gardeners’ World Spring Fair in Beaulieu (1–3 May). Expect artisan eats, street food and seasonal tastings alongside garden inspiration, expert talks and hands-on workshops – plus plenty for little ones, from vintage games and tractors to a ride on the Beaulieu Monorail and the Little Beaulieu adventure play area.

Pop culture fans, this one’s for you: Portsmouth Comic Con returns to Portsmouth Guildhall (2–3 May). Expect a weekend packed with comics, film and TV stars, plus cosplay, panels, gaming and plenty of merch, whether you’re a die-hard Marvel Universe fan or just after a fun family day out.

Feel-good, eco-friendly vibes take over The Furlong Shopping Centre as the Ringwood ECO Fair returns (9 May). Expect a lively mix of stalls, demos and family activities celebrating sustainable living, plus live music and even the chance to snap up a dwarf fruit tree – perfect for anyone looking to go a little greener while they grab a coffee or do a spot of Saturday shopping.

A gloriously quirky, vitamin-packed Hampshire tradition returns as the Alresford Watercress Festival takes over New Alresford (17 May). Expect market stalls, live entertainment and plenty of leafy fun – from catching bunches tossed by the Watercress King and Queen to hopping aboard the Watercress Line – plus the chance to tour a farm and see brave competitors tackle the watercress eating record.

A mini arts festival with big personality lands on the island as Cowes Fringe returns (22–24 May). Expect a packed programme of theatre, live music, comedy and creative workshops, with standout appearances from the likes of Derek Jacobi – plus everything from tribute acts to hands-on community projects and chocolate and wine pairings (we’re in).

And the ultimate doggy day out to end the month: Dogstival takes over the New Forest’s Burley Park (30–31 May) for a tail-wagging weekend of beach-party vibes, from paddle pools and foam parties to agility shows, live music and quirky treats. Think doggy discos, pup-friendly afternoon tea and all-round fun for four-legged friends and their humans.

COMEDY

Like a spot of improv? Quick, chaotic and completely unscripted comedy in Fareham as Shoot From The Hip (8 May) bring their award-winning, TikTok-viral improv show packed with unpredictable games, wild scenes and brilliantly unhinged audience interaction to Fareham Live. No script, no safety net, just fast-paced comedy chaos (for ages 12+).

Also on at Fareham Live, get your seat for a top-tier line-up featuring Jason Byrne, Jo Caulfield and Paul Zerdin, serving up a night of stand-up, sharp wit and brilliantly unpredictable comedy in McIntyre’s Stitches Comedy Club (15 May).

OUTDOOR CINEMA

Screen on the Lawn at Aviator, Farnborough open air cinema Hampshire Top Gun

Popcorn at the ready – the season begins this month. Cinema under the stars gets a luxe twist at Screen on the Lawn at Aviator, Farnborough (22–24 May). Settle in for alfresco screenings of feel-good favourites like Pretty Woman and Grease along with Zootropolis 2 and F1: The Movie, all while private jets glide dramatically behind the screen. (Picnic rug optional, Champagne upgrades encouraged).

MUSIC & DANCE

Jools Holland tour 2026 May Hampshire — Image: Jools Holland and his Rhythm & Blues Orchestra

Join in a night of big band brilliance in Basingstoke as The Anvil hosts Jools Holland and his Rhythm & Blues Orchestra this 15 May. Featuring Roachford and special guest vocalists, expect a high-energy celebration of rhythm and blues from one of the UK’s most engaging live performers. Or catch him the next day (16 May) at Fareham Live.

Ahoy there! Sea shanties, salty air and a proper good singalong await on the Island as the Yarmouth Sea Songs Festival drops anchor on Yarmouth Green (22–25 May). Expect foot-stomping folk tunes, lively performances and a laid-back seaside buzz, with street food, beer tents and plenty of chances to join in the chorus.

And one for the Strictly fans, later in the month, Amy Dowden and Carlos Gu take to the stage at The Anvil, Basingstoke in their self-titled show Amy & Carlos: Reborn (30 May). The powerful dance and opera fusion features live vocals and show-stopping choreography set to crowd-pleasing anthems.

FOOD & DRINK

Street Food Awards 2026 Gunwharf Portsmouth Hampshire May — Image: British Street Food Awards

Take a bao! (Or a wrap, stir fry, burger). Whatever your fave, there’ll be a feast of global flavours on the south coast when the British Street Food Awards returns to Gunwharf Quays (22–25 May). Expect four days of sizzling street food action as top traders battle it out for the public vote – think everything from loaded waffles to flame-grilled ribs – plus live music and all the waterfront shops to browse.

More street food plus live tunes and family fun at The Big Eat Festival at Royal Victoria Country Park (23–25 May). Expect global flavours from top local traders, live music across the weekend and plenty to keep little ones entertained – all with a feel-good twist, as the festival supports local charities and food banks.

Prefer some table service? Enjoy a gourmet, seasonal taste of the New Forest in Brockenhurst at Careys Manor Hotel & SenSpa’s From Field to Fork: A New Forest Food & Wine Experience (8 May). The four-course menu will showcase local produce from The New Forest Fruit Company with expertly matched wines from B58 Winery, alongside a relaxed tasting hosted by the vineyard’s owner.

EXHIBITIONS

Zoe Wilson photographer Rock Legends Live at Palais des Vaches Art Gallery New Forest — Image: Photographer Zoe Wilson’s *Rock Legends Live* exhibition

Rock royalty takes centre stage in the New Forest with the new Rock Legends Live exhibition at Palais des Vaches Art Gallery (now–10 May). This striking work by Zoe Wilson unveils a treasure trove of previously unseen 1980s live music photography, capturing icons like Prince, Tina Turner and Bruce Springsteen in their raw, electrifying prime.

A celebration of creativity in one of Hampshire’s most iconic settings as MADE Winchester takes over Winchester Cathedral this 7–9 May. 100+ contemporary makers will showcase ceramics, jewellery, textiles and more, alongside live demos, talks and hands-on workshops.

And art lovers on the Island, it’s time to get excited. The Isle of Wight Open Studios returns across Isle of Wight (15–25 May 2026). More than 200 artists will open their studio doors, with free access to a colourful mix of painting, ceramics, textiles and more, plus the chance to meet the makers and explore the island’s thriving creative scene.

KIDS

Bear-Hunt-at-The-Vyne © National Trust Images Arnhel de Serra — Image: *We’re Going on a Bear Hunt.* © National Trust Images *Arnhel de Serra*

Swish, splash and squelch your way through a family adventure as We’re Going on a Bear Hunt meets magnificent National Trust big hitter The Vyne near Basingstoke (16 May–28 June). Inspired by the beloved story, We’re Going on a Bear Hunt, this interactive outdoor trail brings the story to life with sensory installations – think swishy grass, oozy mud and a mysterious cave.

Peep, peep! All aboard a classic family favourite as Day Out With Thomas™ rolls into the Watercress Line (23–31 May) for a very special service of train rides with Thomas the Tank Engine, live shows, meet-and-greets, music and more.

What’s on around Hampshire and Isle of Wight this May

You may also like