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Isle of Wight entertainment

On the Isle of Wight it’s impossible to run out of things to do!

When it comes to entertainment, the Island is a hive of activity with events happening every day in every town.

At night the towns and villages come to life as the pubs & bars and bistros & restaurants open up for night time trade.

As you walk through the high streets, you can hear music from local artists being enjoyed inside the various entertainment venues.

As well as being a great place for music (spearheaded by the fantastic Isle of Wight Festival), the Island has a name for itself as a bit of an arts hub.

We have some excellent theatre groups and smaller festivals which celebrate the best of the Isle of Wight’s creative talent.

Plays and films are shown in all kinds of quirky venues, from old converted post offices to 18th century stately homes.

And there is The Wight Proms, a festival of open-air picnic concerts celebrating the Isle of Wight's music, food, people & red squirrels. There has never been a music festival quite like this on the Isle of Wight.

If you’re feeling more conventional, we also have larger cinemas which screen national releases every day.

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The Wayfarer Cycle Touring Club Isle of Wight Randonnee

Type

Type:

Sporting Event

ISLANDWIDE

he Wayfarer Cycle Touring Club Isle of Wight Randonnee is a non-competitive cycle ride established by the Wayfarers in 1985.

Dates

From:

4 May 2025to4 May 2025
Trees of Life Series Gong & Sound Baths - Crab Apple

Type

Type:

Health & Wellbeing

Ventnor

Trees of Life Series Gong & Sound Baths
Introducing a curated series of 4 Sound Journeys focusing on the natural gifts of British trees .
Celebrate Crab Apple's gift of: Trust, guidance and love!
What is a sound bath?
A sound…

Dates

From:

4 May 2025to4 May 2025
Concert performed by The Woodford Singers

Type

Type:

Concert

Ryde

Join The Woodford Singers, an award-winning ladies choir from Essex, for this special concert. Performing classical and contemporary choral music by composers Chilcott, Whitacre and Quartel.
Free entry and all donations to the Abbey.

Dates

From:

5 May 2025to5 May 2025
Music & Tapas with The Aurora Duo (Harp & Flute)

Type

Type:

Music

Newchurch

Join us at The Garlic Farm Restaurant for our monthly tapas & music evenings. We are very pleased to be hosting a series of visiting professional musicians for recitals throughout 2025 in collaboration with Wight Proms Wednesdays.
The restaurant…

Dates

From:

7 May 2025to7 May 2025
Wolverton Folk & Blues Fair

Type

Type:

Festival

Newport

A day long Festival of Folk & Blues set in the stunning grounds of Wolverton Manor in Shorwell.
From the successful launch in 2011, the family friendly festival raises funds to support teenage and young adult Cancer care and for the local…

Dates

From:

10 May 2025to10 May 2025
Isle of Wight Walking Festival

Type

Type:

Walking

ISLANDWIDE

Walk this way! The Isle of Wight Walking Festival will return in Spring 2025 (10th - 18th May) and Autumn 2025 (4th - 12th October).
An event for keen hikers, relaxed wanderers, and curious explorers alike, the Isle of Wight Walking Festival is…

Dates

From:

10 May 2025to18 May 2025

From:

4 Oct 2025to12 Oct 2025
Abbey Brass in Concert

Type

Type:

Concert

Newport

Abbey Brass present music for all tastes including music from the movies, musicals, pop and classical repertoire. Admission is free with a retiring collection.

Dates

From:

10 May 2025to10 May 2025
Mamma Mia Bottomless brunch Singalong

Type

Type:

Music

Newport

Singalong to all the best ABBA hits from Mamma Mia. 2 Hours of singalong with the fabulous Diva-Licious Duo. 90 minutes bottomless Prosecco and 60 minutes delicious Greek Meze food.
A fantastic afternoon of music, Prosecco and food.

Dates

From:

10 May 2025to10 May 2025
Emilio Santoro as Elvis

Type

Type:

Music

Newport

Emilio has been crowned as the 2024 Ultimate Elvis Tribute at Elvis' home of Gracelands in the USA! This means Emilio is now officially the number one Elvis tribute in the world!
Emilio Santoro brings his award-winning Elvis Presley theatre…

Dates

From:

10 May 2025to10 May 2025
Walk the Wight

Type

Type:

Walking

VARIOUS

Walk the Wight, the Island's best fundraiser, is back for 2025!
This year has 3 different routes for you to choose from, with the main 26 mile event seeing you trek from Bembridge Airport all the way to The Needles!
Other, shorter, routes…

Dates

From:

11 May 2025to11 May 2025
Discovering Ventnor with The Royal Hotel

Type

Type:

Guided Walk

VENTNOR

Discovering Ventnor
Discover the rich history of Ventnor and Bonchurch, from their connections to Queen Victoria and Charles Dickens to the unique microclimates that made them renowned for their health benefits.
An Immersive Walking…

Dates

From:

12 May 2025to12 May 2025

From:

16 May 2025to16 May 2025
The Critic - Cowes Film Club

Type

Type:

Film

Cowes

The Critic is an enjoyable and engaging watch and will be shown at Trinity Theatre.
The film is about Jimmy Erskine, The Critic, who is the most feared and famous theatre critic in 1930s London.
If you like quality British cinema with…

Dates

From:

15 May 2025to15 May 2025
Isle of Wight Open Studios

Type

Type:

Arts

Islandwide

Isle of Wight Open Studios continues to grow as a cornerstone of the Isle of Wight’s cultural calendar and following the success of this year’s much-loved IW Open Studios - which saw over 120 artists participating – along with artists valuable…

Dates

From:

16 May 2025to26 May 2025
Jack Up Events presents Legend - The Music of Bob Marley Live

Type

Type:

Music

SHANKLIN

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. Combining his superb, distinctive…

Dates

From:

16 May 2025to16 May 2025
Forever Jackson

Type

Type:

Music

Newport

Forever Jackson is the world's premiere MJ production, setting the industry alight with critically-acclaimed sell-out shows around the world. Awarded 'No.1 UK Michael Jackson Tribute Show', the show has since become one of the most in-demand in the…

Dates

From:

16 May 2025to16 May 2025
Isle of Wight Open Studios 2025

Type

Type:

Arts

Join us as we celebrate the vibrant creativity of Isle of Wight artists for the annual Open Studios event!
Steeped in a rich history of fostering community and creativity, the event opens doors — quite literally — to the vibrant studios of…

Dates

From:

16 May 2025to26 May 2025
Festival of Transport at Isle of Wight Steam Railway

Type

Type:

Festival

Havenstreet

Certified motorheads will get revved up about this brilliant festival of cars, lorries, bikes and trucks!
There's something for every vehicle fan, be it a vintage pride and joy to a brand new hot rod.
Switch from road to rail and climb…

Dates

From:

18 May 2025to18 May 2025
Busy Bee Gong & Sound Bath - Niton

Type

Type:

Health & Wellbeing

Niton

Celebrating Bee Day! This one is for all the Busy Bees out there. Take time out, and switch, off at this beautiful evening sound bath with gongs, bowls, chimes at this gorgeous space at Chapel Studio in Niton, Isle of Wight. Join me for aa…

Dates

From:

22 May 2025to22 May 2025
Cowes Fringe

Type

Type:

Festival

Cowes

This dynamic fringe event in this part of the Isle of Wight will deliver an explosion of art and culture through performances and workshops. Hosted in unique venues throughout the town in Cowes, Cowes Fringe guarantees a memorable weekend…

Dates

From:

23 May 2025to25 May 2025
Family Farm Tours May 2025

Type

Type:

Tour

Newchurch

Daily at 11am from 24th to 31st May
Join one of the family members who run the farm for a short walking farm tour and learn all about what we do here: garlic growing, farming practices, woodland management, agroforestry, our WETland ecosystem and…

Dates

From:

24 May 2025to31 May 2025