Things to do

Isle of Wight festivals

With walking festivals for the outdoor types to fringe festivals for the artists among us, the Isle of Wight has plenty on offer during festival season. We’re particularly excited for the Isle of Wight festival line-up this year as we’ve previously seen Bastille, The Who, Razorlight and even Bon Jovi grace the stages. For music-lovers, this promises to be the festival of the year.

But for those looking for something a little bit different, there are a few festivals throughout the year which will certainly bring you new experiences by the bucket load. Arts, walking, nature, sailing and discovery all wait for those who seek it on the island this summer.


Isle of Wight Walking FestivalThe Isle of Wight walking festival makes the most of the 500 miles of paths on the Isle of Wight.

9th - 22nd October 2021

The popular festival returns once again this spring with local walkers and visitors invited to set off across the island. There are walks for all ages and abilities available, including guided and self-guided routes to follow at your own pace. Over 500 miles of well-kept footpaths and 60 miles of dramatic Heritage Coastline, there’s plenty to explore.


Isle of Wight Festival

16th - 19th September 2021

The first IOW festival dates back to 1968 and since then has hosted names like Bob Dylan and Jimi Hendrix. With huge themes each day and plenty of opportunities to get decked out in your latest festival attire, this is the ultimate fun weekend away with friends.


Cowes WeekThe Cowes Week regatta is an amazing spectacle of sailing on the Isle of Wight.

31st July - 7th August 2021

A huge event in the British sporting calendar, Cowes week brings sailors from around the world to the island. With up to 40 daily races and up to 800 boats taking part, this is a spectacle for anyone staying on the Isle of Wight. There’s a great mix of sailing and social events on shore, head to Cowes for live entertainment and parties all week long.


Isle of Wight Pride

16th July 2022

The Isle of Wight is hosting the next UK Pride. Held in the seaside town of Ryde, overlooking the Solent, this fun, inclusive and welcoming event provides the perfect excuse for celebrating. Enjoy a long weekend by the beach with fresh local food, live music and a colourful celebration of the LGBT community.


Ventnor FringeThe view over Ventnor haven on the south of the Isle of Wight.

23rd - 1st August 2021

The Fringe attracts emerging talent from a whole host of genres, performing across several venues in Ventnor on the south of the island. The line-up has been carefully curated to include some of the most exciting acts from across the UK and beyond. It’s free to attend but some of the shows are individually ticketed. Operating out of the best creative hub on the island, the Ventnor Exchange, this promises to be one of the coolest festivals you attend all year. 


Isle of Wight Literary Festival

8th - 10th October 2021

Based at the atmospheric Northwood House in Cowes, the literary festival is made for book-lovers. With an exciting line-up of speakers, authors and events, this weekend will have you feeling incredibly civilised and cultural by the end.


Stay in one of our Isle of Wight holiday cottages.

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