What’s On

From a major music festival to sailing and walking events, from a classic car show and scooter rally to a weekend talking books, the Isle of Wight certainly knows how to throw a party!

29-31 MaySky High Glow

Robin Hill, Newport

Hot air balloon enthusiasts should flock to this innovative country park near Newport for spectacular Night Glow displays accompanied by live music.


30 May – 6 June Isle of Wight Festival of Running


Now in its fourth year, the festival has become one of the biggest sporting events on the island, as you skirt over dramatic cliffs, round beautiful coves and past a world-famous pop festival site. The festival features 5k races, junior fun runs and on Sunday, 6 June, more than 400 runners will take on the Needles Half Marathon, one of the toughest trail runs in the UK. The route features spectacular scenery – Colwell Bay, the Needles Rocks, Tennyson Down and Freshwater Bay (Colwell Bay and Freshwater Bay are good places to cheer the runners on!). It is too late to take part this year, but the 2022 event is already in planning.


31 May – 4 JuneDinos vs Cowboys

Blackgang Chine, Nr Chale

Watch some of this much-loved amusement park’s key characters go head-to-head in the ultimate popularity battle.


4-6 JuneIsle of Wight Steam Railway 50th anniversary gala

Isle of Wight Steam Railway, Havenstreet

Celebrate 50 years of the Isle of Wight Railway with three steam locomotives in action each day. Other activities include evening train rides and an early morning ‘newspaper’ train.


5-6 JuneDrive-In Cinema

Sandown Airport, Sandown

It’s back, playing your favourite films on a giant LED screen at the new location of Sandown Airport – and it’s all for a good cause.


26-27 JuneReal Ale Festival

Isle of Wight Steam Railway, Havenstreet

Real ale and rides on old steam trains, what’s not to like? Try local beers from Yates, Goddards and Island Brewery alongside ales from the mainland at the 16th Isle of Wight Real Ale Festival.


3 JulyRound the Island Race

It’s the 90th anniversary for this legendary race, one of the sailing world’s greatest spectacles. Get your pitch early and watch the 1600-plus range of crafts storm past The Needles.www.roundtheisland.org.uk

3-4 JulyThe 1940s Experience

Isle of Wight Steam Railway, Havenstreet

Inspired by the music and dance of the 1940s. Expect lindy hoppers, songs from the swing era and even a ukulele performance or three


18 July – Rainbow Run 2021

Sandown Airport

Walk, run or dance your way through the Isle of Wight’s happiest 3K by taking part in Wessex Cancer Trust’s Rainbow Run 2021! The family fun run will feature giant inflatables, powder paint and, new for the charity’s 40th birthday year, two brilliant bubble stations! Sign up at the link below if you want to take part…


23 July – 1 AugustVentnor Fringe

Ventnor Exchange, Ventnor

One of the UK’s most popular fringe festivals, the multi-venue event features over 400 emerging artists from across the UK and beyond. It’s based in venues that range from churches to warehouses, launderettes to barber shops.  This year the event is running for longer than normal to accommodate a greater number of performances in smaller venues. The Fringe HQ – Ventnor Exchange – is a dynamic creative hub, combining a craft beer bar and record store and it’s open year-round.


31 July – 6 AugustCowes Week


Watch top yachtsmen and women doing their highly skilled thing on the water at one of the world’s premier yachting events, and then enjoy the party back on the land. The highlight promises to be SailGP, with boasts world record-breaking speeds, and last saw crowds of more than 24,000 turn up to watch the action with a total global audience of more than 230 million.


6-8 AugJack up the Summer Vol.8

North Fairlee Farm, Nr Newport

This family-friendly throwback festival features household name artists from the 80s and 90s and takes place at North Fairlee Farm, near Newport. This year expect blasts from the past that include Heaven 17, Heather Small, Aswad and Hugh Cornwell.


21-22 AugustGarlic Festival


Tickle your taste buds with garlic sweetcorn, garlic beer and even garlic ice cream and garlic fudge at this fun filled weekend of entertainment near Sandown.


26-30 AugustIsle of Wight Scooter Rally Weekender


Over 5000 scooters descend on the Island every year for this event, which sees a switch in venue to Sandown Airport (though doubtless many will continue to congregate on Ryde seafront).


27-30 AugustThe Island Steam Show 

Isle of Wight Steam Railway, Havenstreet

Now in its 46th year, this action-packed event is a great family day out, with traction engines, games, vintage cars and motorcycles, and ancient wagons. Plus there are fairground rides, live music, food stalls and real ale.


27-29 AugCowes Powerboat Races


Feel the throb as the legendary 200-mile Cowes-Torquay-Cowes powerboat race returns to rule the waves and thrill spectators.


4-5 SeptemberWolverton Manor Garden Fair


Everything a traditional village fair should be, with exhibits, crafts, garden nurseries, music, cider and hay bales.


11-12 SeptemberIsle of Wight Classic Car Extravaganza

Esplanade, Ryde

Now in its 19th year, the event held in Ryde will show off ancient vehicles motoring in from all over Europe.


12 SeptemberWalk the Wight 

Island Wide

Or Walk the Wight Your Way. Either way, Earl Mountbatten Hospice’s inspiring yomp (or stroll, if you prefer to go at a slower pace) attracts thousands of people, who stride out together across the beautiful Isle of Wight countryside to help those in need.


16-19 SeptIsle of Wight Festival

Seaclose Park, Newport

The most exciting weekend of the summer on the Island, the Isle of Wight Festival continues to build on its proud heritage with show-stopping headliners such as Foo Fighters, The Rolling Stones, Jay-Z, Coldplay and Fleetwood Mac. This year headline acts include Liam Gallagher, Tom Jones, Snow Patrol and David Guetta, with Duran Duran heading up the main stage on Sunday night. The festival boasts an impressive age range, too, from babes in arms to grizzled old rockers – in short, everyone is catered for, which is one of the festival’s main strengths. While the focus is on the main stage and the big top line-ups, there is plenty more fun to be had in other areas, from Isle of Wight bands to Island-brewed ales.


9-10 OctoberIsle of Wight Literary Festival

Northwood House, Cowes

Head to the historic, magnificent Grade II-listed Northwood House in Cowes for a seriously impressive line-up of writers and speakers that have numbered explorers to poets.


22-26 OctoberHarp on Wight International

Ryde Methodist Church , Garfield Road, Ryde

This is the eighth year for this prestigious gathering of leading harpists and in addition to a series of concerts, which offer a myriad of styles, there are informative teaching workshops.