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!
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 annual Round the Island Race is a one-day yacht race around the Isle of Wight. The spectacle regularly attracts over 1,000 boats and thousands of sailors, making it one of the largest yacht races in the world!
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.
Chale Show
With an incredible mix of entertainment, attractions, and live music, Chale Show makes for a fun, family-friendly day out.
From motorbike and quad stunt shows, to sheepdog and duck displays, there'll be something for everyone to enjoy!
Cowes Week
For 200 years, Cowes Week has been a world-famous rite of passage for any sailing enthusiast, and a real celebration of the sport.
Pier2Pier Sea Swim IOW 2026
The Pier2Pier Sea Swim Isle of Wight is a 1.8 mile open water event organised by the Isle of Wight Marlins Swim Club.
Isle of Wight Scooter Rally
This August Bank Holiday, scores of scooterists will once again take over the Island in a spectacle like no other!
Wightrider
The Isle of Wight Bus and Coach Museum are presenting their Wightrider weekend on Saturday 11th and Sunday 12th October 2025.