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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-Sep 24-13
steamship shieldhall at sea with dress flags
Entertainment

Summer Sailings on SS Shieldhall

Join Steamship Shieldhall on one of her summer excursions to the Solent, and experience the glamour and tradition of steam at sea! 

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
Jun 7
taylor swift and harry styles tribute acts pose together
Music

Jack Up Events presents: Swift & Styles – The Tribute Concert

Get ready for a show like no other with The Ultimate SWIFT & STYLES Tribute Concert!

Ryde 5:30 - 11pm
Jun 7
black and white portrait photo of radio 1 dj charlie hedges
Entertainment

Sunset Sessions Presents Charlie Hedges

Join in the hottest party of the summer as BBC Radio 1 DJ Charlie Hedges takes to the stage on the clifftop of Blackgang Chine!

6:30 - 11:59pm
Jun 8
a group of smiling women in matching pink charity t shirts and walking gear
Walking

Breast Walk Ever Hampshire

Walk for life-saving research into breast cancer, whilst taking in the splendour of the South Downs Area of Outstanding Natural Beauty!

All Day
Jun 13
darts in the bullseye of a darts board
Entertainment

An Evening with James 'The Machine' Wade

Spend an evening in the presence of darts legend James Wade as he visits the Island this June!

6 - 11pm

Customer Reviews

1 2 3 4 5
All went to plan, no problems. Staff always polite and helpful.
Booking process was a reasonably smooth, just had to remember and confirm, where I was sailing from.
Tue, May 27 2025
1 2 3 4 5
Excellent. Efficient loading and unloading at both ports. Ships were clean and comfortable. We will certainly use the service again
Fri, May 23 2025
1 2 3 4 5
Good service and a good crossing
Wed, May 21 2025