Which is lucky, as the summer calendar here is jam-packed with them. From classical music and a celebration of the arts to a weekend dedicated to garlic - there truly is something for everyone on the Island. Struggling to decide? Read through our handpicked top choices for the best festivals on the Isle of Wight…

Ventnor Fringe, Ventnor

Friday the 18th to Sunday 27th of July

Best for: Arts and culture 

The Island's biggest arts festival, Ventnor Fringe, will see some 150 different shows take place over 10 days. This year's shows are yet to be revealed, but previous years have seen everything from showstopping circus performances to cutting-edge cabaret. 

The main festival site sits in Ventnor Park, which transforms into 'Festival Village' with Big Tops and other tents housing performances. Ventnor Fringe is an eclectic festival, and you can expect events to take place in nearby ancient churches, underground bunkers, and even a 1930s Parisian bus.

Children are welcome and well-behaved dogs can come along for the fun (just not at performances inside tents). Check out holiday cottages in Ventnor and start planning your festival itinerary now.

The Wight Proms Festival, Cowes

Tuesday the 12th to Sunday the 17th of August, 2025

Best for: Classical music buffs 

If you like your musical classical, look no further than The Wight Proms Festival, which promises a six-day celebration of opera and orchestral music. As well as classical music aplenty, you can expect comedy, drag, dance, country music, musical theatre and more. 

Set in the manicured lawns of Northwood House, a Grade II listed manor house dating back to 1799, the stunning surrounds make for an opulent festival backdrop. It’s a family-friendly festival, with music aimed at kids - apart from comedy night, which is for adult ears and eyes only. 

Pack your picnic blanket, but leave tables and gazebos at home. There are a few seated spots, but they’re taken on a first-come first-serve basis. You’ll also find disabled access throughout, with wheelchair and carer tickets available to purchase. Why not browse holiday cottages in Cowes and start planning your festival trip today?

The Isle of Wight Garlic Festival, Nr Newchurch

Saturday the 16th to Sunday the 17th of August

Best for: Garlic lovers

Since its inception in 1983, The Isle of Wight Garlic Festival has taken place on the third weekend of August at The Garlic Farm at The Fighting Cocks Crossroads, just outside of Newchurch. Aside from garlic, (more in a moment) visitors young and old are in for a weekend of star chef demonstrations, tastings, live music, games and children's entertainment including a fun fair. 

But make no mistake, the star of the show here is undoubtedly garlic and visitors can enjoy it in seemingly unending varieties including garlic biscuits, fudge, popcorn and ice cream. Wash it all down with a pint of something delicious in the beer tent, or head to the tea tent for more afternoon tea vibes. It’s just 5 miles down the road to the pretty seaside town of Shanklin, the perfect base for your galicky adventures. 

Isle of Wight Festival, Newport

Thursday the 19th to Sunday the 22nd of June

Best for: Epic headline acts

If you're after big festival vibes on the Island, it's got to be the Isle of Wight Festival near Newport, famed for its epic line-up and iconic atmosphere. This year headliners include Sting, Stereophonics and Justin Timberlake, as well as acts like Busted, Texas, Clean Bandit and Example. 

With around 55,000 festival revellers turning up each year, this is no small Island event. And while the festival isn't aimed at children, past years have included a kidzone with talent shows, circus workshops, and family-friendly shows, as well as a wild play area with mud kitchens and a sensory space to offer some peace and calm. 

Not a fan of the camping side of festivals? Explore holiday cottages in Newport or nearby Merstone if your idea of a good time is dancing until you drop…into a comfortable bed.

Isle of Wight Walking Festival, various locations

Saturday the 10th to Sunday the 18th May + Saturday the 4th October to Sunday 12th October

Best for: walkers and outdoorsy types

If a traditional festival isn't for you, check out the Isle of Wight Walking Festival, which runs twice a year in spring and autumn. Celebrating its 26th year in 2025, it's a celebration of the great British outdoors, with relaxed strolls through pretty scenery and challenging hikes to satisfy curious explorers. 

With a range of routes to suit all ages and abilities, this festival offers visitors a unique chance to be guided through some of the best walks on the Island while taking in the arresting landscape, steeped with history and rich wildlife. 

With walks taking place across the Island, you could choose a base anywhere. Explore some of the best holiday cottages in the coastal village of Brembridge or head to the rugged cliffs and open countryside on West Wight and pick a place in Freshwater.

Chale Show, Chale

Saturday the 2nd to Sunday the 3rd of August

Best for: Village fete vibes 

Picture a village fete and a big arena event, then imagine a crossover and you’ve got Chale Show! The horticultural marquee is a big deal here, with 1,500 entries across 240 categories (yes, it's a big marquee) including vegetables, floristry, and cookery. 

For bigger thrills, head to the main arena for hairraising stunts, falconry flying, and magic shows. The Mountbatten Sunflower Music Stage showcases some of the best homegrown talent on the Island, while the Somewhenever Story Tent is the place to get in touch with your creative side.

Looking for a bolthole to base yourself? Check out Brightstone, often referred to as the prettiest village on the Isle of Wight, it’s rather conveniently only 6 miles up the coast from Chale.

Cowes Week, Cowes

Saturday the 2nd to Sunday the 8th of August

Best for: Watersports fanatics 

The oldest and biggest sailing regatta in the world, there is nothing quite like Cowes Week. Dating back to 1826, this popular fixture in the British sporting calendar now stages around 40 daily races for almost 750 boats, featuring everyone from Olympic professionals to weekend sailors. 

The event attracts close to 100,000 spectators each year, who attend not only to watch the races but enjoy the parties, live entertainment, and unique atmosphere. Enjoy the largest sailing regatta in the world in style and book a holiday cottage in Cowes.

Dreaming of a fabulous festival by the sea? Peruse our selection of Isle of Wight cottages and start planning your next Island adventure now.