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!
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.
Summer in Nashville
The BIGGEST Nashville party to hit the UK is coming back to the Isle of Wight on Sunday the 5th July 2026! Get ready for a big Country music themed bash featuring artists from the USA, amazing BBQ food and more.
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.
Proms '26
Have your flags at the ready and don’t miss your chance to be part of this special occasion!
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.
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.
Festival of Heroes
Festival of Heroes returns to Brading Roman Vill this July with all your favourite characters who can't wait to meet you!