Isle of Wight entertainment

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1. 

   

   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
2. 

   

   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
3. 

   

   Fearlessly Taylor

   Type

   Type:

   Music

   Newport

   Step into the spotlight with Fearlessly Taylor as they present an exhilarating tribute to the one and only Taylor Swift. Get ready to be swept away on a whirlwind journey through Taylor's legendary career, with show-stopping replica costumes,…

   Dates

   From:

   30 Oct 2025to30 Oct 2025
4. 

   

   Christmas Fair at Isle of Wight Bus & Coach Museum

   Type

   Type:

   Christmas

   RYDE

   Get into the festive spirit at the Isle of Wight Bus & Coach Museum's magical Christmas Fair on Saturday 1 November.

   Wander through the charming seasonal stalls filled with gifts and festive treats. Feel the joy and excitement as your little…

   Dates

   From:

   1 Nov 2025to1 Nov 2025
5. 

   

   Princess Live!

   Type

   Type:

   Family

   Newport

   Princess Live! is the ultimate hour long princess pop party, featuring your favourite fairytale royalty in this all singing all dancing hour long concert show.

   The Princesses are tired of their royal duties. So they decided to come together and…

   Dates

   From:

   2 Nov 2025to2 Nov 2025
6. 

   

   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
7. 

   

   A Tribute to Sting and The Police staring The Rozzers

   Type

   Type:

   Music

   Newport

   Fronted by Sting look and sound-a-like Owen James and his band 'The Rozzers', 'A Tribute to Sting & The Police' is the most authentic Sting tribute in Europe. The band have performed all over the world for several years and now embark on their…

   Dates

   From:

   15 Nov 2025to15 Nov 2025
8. 

   

   Festive Fun at Osborne

   Type

   Type:

   Christmas

   East Cowes

   Christmas activities and festive fun at Osborne Visit Osborne this Christmas season for a barrel of laughs and festive fun!

   Enjoy festive activities including storytelling and music.

   Dates

   From:

   29 Nov 2025to21 Dec 2025
9. 

   

   An Evening with Football Legend Neil 'Razor' Ruddock - Isle of Wight

   Type

   Type:

   Talks

   Newport

   Don't miss the chance to see football legend Neil Ruddock in an exclusive live interview and audience Q&A, hosted by the renowned Sports and Entertainment presenter Kenzie Benali, having presented live at some of the biggest competitions in global…

   Dates

   From:

   29 Nov 2025to29 Nov 2025
10. 

    

    Fawlty Towers Comedy Dining Event

    Type

    Type:

    Comedy

    Shanklin

    New Fawlty Towers show The Fawlty Towers Gang are back with an hilarious new show. Join us at Luccombe Hall Hotel on 29th November for an unforgettable Fawlty Towers Comedy Dining Experience!

    Food, drinks and entertainment Enjoy a…

    Dates

    From:

    29 Nov 2025to29 Nov 2025
11. 

    

    Christmas Party Nights at The Royal Hotel

    Type

    Type:

    Christmas

    Ventnor

    Join us for a delicious Christmas dinner in our 2 AA Rosette Geranium Restaurant, where you'll enjoy a festive party ambiance and a lively dance floor with all your favourite songs from Island DJ Tony Martin.

    The Royal Hotel, adorned in all its…

    Dates

    From:

    29 Nov 2025to20 Dec 2025
12. 

    

    Murder Mystery Christmas Dining Event

    Type

    Type:

    Competition / Game

    Shanklin

    A Night of Mystery, Murder & Mayhem! Step into a world of suspense and deception as your evening of murder and intrigue begins at 6:45 pm in The Bishops Bar, where a glass of fizz awaits. As you mingle with fellow guests, keep your wits about you,…

    Dates

    From:

    6 Dec 2025to6 Dec 2025
13. 

    

    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
14. 

    

    Xmas Party Night Vol 1

    Type

    Type:

    Christmas

    Shanklin

    Celebrate your Christmas with a jam packed party at the Shanklin Hotel featuring UK no1 Kylie Tribute and Party Anthems Sax, Vocalist Celena.

    Doors open 19:00 hrs. Limited free parking. Sit down meal option. Rooms available for night £30.00.pp…

    Dates

    From:

    6 Dec 2025to6 Dec 2025
15. 

    

    Steeleye Span

    Type

    Type:

    Music

    Newport

    Together for fifty six years now, Steeleye Span changed the face of folk music forever by taking it into the world of gold discs and international tours. Now they return with Conflict, their first full studio album in over five years. All…

    Dates

    From:

    6 Dec 2025to6 Dec 2025
16. 

    

    Xmas Party Night Vol 2

    Type

    Type:

    Christmas

    Shanklin

    Celebrate your Christmas with a jam packed party at the Shanklin Hotel featuring UK no1 Abba Tribute and party DJ Dave Hollidge

    Doors open 19:00 hrs. Limited free parking. Sit down meal option. Rooms available for night £30.00.pp per night…

    Dates

    From:

    13 Dec 2025to13 Dec 2025
17. 

    

    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
18. 

    

    Christmas at The Royal Hotel

    Type

    Type:

    Christmas

    Ventnor

    A Christmas Break To Remember
    3 nights from £850.00 per person | 4 nights from £975.00 per person

    23rd - Saturday 27th December 2025
    The Royal is delighted to offer you the finest hospitality and festive entertainment, in the elegant setting of our…

    Dates

    From:

    23 Dec 2025to29 Dec 2025
19. 

    

    Isle of Wight Festival

    Type

    Type:

    Festival

    Newport

    The award winning Isle of Wight Festival is steeped in history and famed for mixing iconic legendary artists with the hottest up and coming acts.

    Dates

    From:

    18 June 2026to21 June 2026

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