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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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Ryde Carnival Illuminated Procession

Type

Type:

Carnival

RYDE

The very last carnival of the summer, Ryde Carnival's illuminated procession is a fabulous spectacle of light and music that rounds the Isle of Wight carnival season off in style.

Join the crowds and take in the atmosphere as the carnival parades…

Dates

From:

30 Aug 2025to30 Aug 2025
Cider & Cheese Festival @ Isle of Wight Steam Railway

Type

Type:

Food

HAVENSTREET

A regular in the Railway's events calendar.
Get set to sample a whole host of various cheeses perfectly paired with crunchy pickles and tangy chutneys. It's the perfect accompaniment to a cool glass of cider, and with over 25 varieties to try,…

Dates

From:

6 Sept 2025to7 Sept 2025
Isle of Wight Steampunk Festival

Type

Type:

Festival

Ryde

Following last year's success, join us to find out what all the excitement is about for the biggest and best Isle of Wight Steampunk Festival 2025 in Ryde. There will be two full days of splendidness between the 26th and 28th September! Embrace your…

Dates

From:

26 Sept 2025to28 Sept 2025
Isle of Wight Literary Festival

Type

Type:

Literature

COWES

A popular annual event in the Isle of Wight calendar, the Isle of Wight Literary Festival will be held between the 9th and 12th October 2025 at Northwood House, Cowes. The festival will once again be providing a varied and exciting programme with…

Dates

From:

9 Oct 2025to12 Oct 2025
Beer & Steam @ Isle of Wight Steam Railway

Type

Type:

Festival

HAVENSTREET

Head to the Isle of Wight Steam Railway's Autumn beer festival for a celebration of beer and steam.
Choose from a huge selection of real ales, there are even a few ciders for those with a sweeter tooth.
You’ll have the opportunity to try…

Dates

From:

11 Oct 2025to12 Oct 2025
Music & Tapas with Kate Robey and Christopher Sheldrake (Cello & Piano)

Type

Type:

Music

NEWCHUCH

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…

Dates

From:

15 Oct 2025to15 Oct 2025
Wizard Weeks @ Isle of Wight Steam Railway

Type

Type:

Heritage & History

HAVENSTREET

It's wickedly wonderful half term fun as witches and wizards cast their magic spell and takeover the Railway.
Follow the spooky treasure hunt trail then climb aboard the spooky steam train. Meet the witch wandering the platform... does she have…

Dates

From:

18 Oct 2025to31 Oct 2025
Halloween Themed Family Supper with Magical Entertainment

Type

Type:

Halloween

NEWCHURCH

Come and have a spooky supper with us and be entertained by the brilliant Huxley Magic.
Table bookings from 6pm.
Book here: https://www.thegarlicfarm.co.uk/pages/the-restaurant

Dates

From:

29 Oct 2025to29 Oct 2025
Ronnie, Reggie and Me - Fred Dinenage

Type

Type:

Talks

SHANKLIN

The definitive insight into the real lives of Britain's most notorious gangsters, from their trusted official biographer. For decades they were feared as the ultimate criminal gang lords of the London underworld, but their reign of terror came…

Dates

From:

30 Oct 2025to30 Oct 2025
Music & Tapas with Phantasia (Theorbo, Mandora & Violin)

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:

5 Nov 2025to5 Nov 2025
Santa Specials at Isle of Wight Steam Railway

Type

Type:

Christmas

HAVENSTREET

Join us for a traditional festive event for all the family.
Ride the train, explore the winter wonderland and visit Santa in his grotto.
Watch the live entertainment and ride the traditional fairground rides. Every child receives a…

Dates

From:

6 Dec 2025to7 Dec 2025

From:

13 Dec 2025to14 Dec 2025

From:

20 Dec 2025to24 Dec 2025
West Wight Chilly Hilly

Type

Type:

Sporting Event

Freshwater

West Wight Chilly Hilly is back in 2025 on Sunday 14th December!
What better way to begin winter festivities than with a 10 mile run in the spectacular West Wight countryside? Taking in cliff paths, beaches, wooded glades and spectacular…

Dates

From:

14 Dec 2025to14 Dec 2025