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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
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 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
Jun 14-15
two glasses of gin and tonic with sliced lime garnish
Food & Drink

Gin & Steam at IW Steam Railway

Join IW Steam Railway for a celebration of gin & steam, with fabulous craft and new gins, rums and vodkas, and enjoy samples as part of your ticket from an array of onsite craft distillers! 

Havenstreet All Day
Jun 14
marquees and crowds with stately wolverton manor building in the background
Arts, Crafts & Culture

Shorwell Midsummer Fair

The 63rd annual Shorwell Midsummer Fair returns to the beautiful grounds of Wolverton Manor!

1:30 - 5pm
Jun 15
cyclists with the sea in the background
Cycling

Ride of Champions

The Ride of Champions is calling all elite riders to take on the ultimate challenge – a gruelling 100-mile journey designed to test your endurance, strength and determination!

Island Wide All Day
Jun 19-22
Festival stage lit up in the dark with confetti
Entertainment

Sky Presents the Isle of Wight Festival 2025

Sky Presents the Isle of Wight Festival 2025 will take place from Thursday 19 to Sunday 22 June! Book your festival ferry travel today!

Newport All Day
Jun-Jul 28-6
children sitting round for a story telling session in the woods
Entertainment

Isle of Wight Biosphere Festival

Enjoy nature and community events for the whole Island, celebrating our UNESCO Biosphere Reserve!

Island Wide All Day

Customer Reviews

1 2 3 4 5
It was good I got there alive
Sun, Jun 1 2025
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