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Events on the Isle of Wight

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!

Event Calendar

Location
Category
May 16
legend - bob marley tribute on stage
Music

Jack Up Events presents: Legend - The Music of Bob Marley Live

When you think reggae, there is only one name that comes to mind! Legend – the music of Bob Marley is an unforgettable evening celebrating this musical icon in one fantastic stage show extravaganza.

7:30 - 9:45pm
May 17-18
rydabus
Spectator Sports

Rydabus

The Isle of Wight Bus and Coach Museum are presenting their Rydabus event weekend on Saturday 17 and Sunday 18 May.

Ryde All Day
May 18
IOW Takeover
Entertainment

Isle of Wight Takeover

Now in its 10th year, enjoy a family-friendly festival of motoring at Robin Hill Adventure Park!

All Day
May 23-25
stage with busy crowd
Entertainment

Cowes Fringe

SAVE THE DATE! Following a very successful 2024, Cowes Fringe is back even bigger for 2025!

Cowes All Day
May 24-25
a red first place rosette ribbon
Entertainment

Isle of Wight Dog Festival

Round up your pack and head to the Island's only festival dedicated to our four-legged friends!

Cowes All Day
May 24-31
actor in cowboy costume firing a gun
Entertainment

Wild West Week at Blackgang Chine

Yeehaw! There’s a buzz around Blackgang Chine as Wild West Week rolls into Cowboy Town! 

All Day
Jun 1
retro car bumper
Entertainment

Cowes Classics Day

Cowes Classics Day is a day to celebrate the past and revive nostalgic memories, with classic cars, famous aircraft, yachts and motor boats on display for all to enjoy.

Cowes All Day
Jun 7
yachts on the water with large colourful sails
Sailing

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!

Island Wide All Day
Jun 7-8
a sheepdog running with farmer in the background
Spectator Sports

Isle of Wight Sheepdog Trials

Bring your picnic blankets and enjoy a FREE family-friendly weekend at the Isle of Wight Sheepdog Trials in Havenstreet!

Havenstreet All Day

Customer Reviews

1 2 3 4 5
Very good
Tue, Apr 1 2025
1 2 3 4 5
See previous comments.

The crossing is far too expensive, though. You won't get 5 stars at that price.
Mon, Mar 31 2025
1 2 3 4 5
No issues with service
Sat, Mar 29 2025