Pack your island holiday with fun things to do
The Isle of Wight is one of the UK's most exciting destinations for festivals and events! There's a wide variety of year-round activities and events, including one of the UK's biggest and best known music festivals, the world's oldest sailing regatta, and a food festival dedicated to one of our most famous exports, garlic!
Isle of Wight Biosphere Festival
Find hidden gems, unearth expert local knowledge and enjoy our beautiful and vibrant island nature.
Red Squirrel Ride
Unlike many challenge events, the Red Squirrel Ride is largely traffic-free, making extensive use of the Island’s extensive network of old railway paths and cycle trails. Choose between two circular routes – 34 and 16 miles.
Jack Up Events presents Dancing Queens & Boyband Dreams
Retro Staycations, the Isle of Wight’s award-winning glamping retreat and vintage campsite, is set to host a spectacular summer weekender packed with music, nostalgia, and festival vibes.
Round the Island Race
The iconic Round the Island Race is one of the largest of its kind in the world. Regularly attracting over 1,200 boats and around 10,000 sailors, it’s one of the UK’s biggest sports participation events.
Classic Isle presents: Proms ‘26
Pack your picnic, settle into a sunny spot and enjoy an unforgettable night of classical music from the Bournemouth Symphony Orchestra.
Classic Isle presents: A Night at the Movies
Experience the magic of the movies as the Bournemouth Symphony Orchestra performs some of the most recognisable and beloved film music ever written.
The 2026 Special Evening of Opera
Enjoy a special evening at the opera in support of Polly’s Fund, led by professional Italian singer and conductor Andrea Colombini as he presents “An Evening at the Opera" in Cowes and Yarmouth.
Wytwoods Festival
Bringing you multiple bespoke stages and a curated dance music lineup including Max Dean, Prospa, Sidney Charles, Alisha, Dr Banana, Jamback, Wheats - plus 50+ additional artists. They will also be hosting two days of wellness and arts classes and takeovers.
Ventnor Fringe
Discover the best new music, comedy and theatre at the Isle of Wight's largest arts festival, Ventnor Fringe. Taking place over 10 days the festival transforms the Island's southernmost town and surrounding coastline to become a stage for hundreds of performances, with venues in even the most unlikely locations.