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La Bouche Manouche featuring Irene Serra

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Entertainment in the Windsor area

We want you to enjoy every moment of your stay in the Windsor and Maidenhead area, however you like to be entertained! With superb art centres, a bustling theatre and plenty of venues hosting exceptional live entertainment, read on for some of our top tips that we hope will keep you most amused.

Enjoy arts and culture in Windsor and Maidenhead

In Windsor we have the thriving Theatre Royal Windsor, a beautiful Edwardian theatre nestling in the shadow of Windsor Castle. The Theatre Royal shows a wide range of live performances including comedy, tragedy, ballet, one-nighters, musicals, theatre, tribute bands, thrillers and the ever-popular annual pantomime!

We have two lively arts centres – Norden Farm in Maidenhead and the Old Court in Windsor – offering a whole host of great events including live comedy and theatre, film and music.

Visit our Theatres page to find out more.

Discover live music

Other Space Arts is a vibrant grassroots venue bringing together original live music, contemporary arts and plant-based food in the heart of Windsor. Housed in a beautifully-restored industrial space, just a short walk from the town centre, Other Space Arts offers a unique cultural experience for both locals and visitors.

Every autumn Windsor Festival and Fringe Festival both feature a diverse programme of live music.

Throughout the year venues such as Eton College School Hall, the Farrer Theatre, Windsor Parish Church and St George’s Chapel become venues for a wide range of concerts by fantastic local orchestras and choirs.

Windsor’s Old Ticket Hall proudly promotes itself as the only venue in town dedicated to live music five days a week.

Enjoy some comedy

Norden Farm, the Old Court and Theatre Royal Windsor are smaller and more intimate spaces, perfect for comedians who are testing their comedy material before heading out on bigger arena tours. Many top names come to Windsor and Maidenhead, including Greg Davies, Russell Howard, Reginald D Hunter, Sarah Millican, Omid Djalili and Jenny Eclair, and you’ll discover many up-and-coming comedians too.

Explore the nightlife

Ascot, Eton, Windsor and Maidenhead all have various options including some fantastic pubs and bars as well as clubs open until the early hours. Read all about nightlife in the Royal Borough.

Experience a trip to the cinema

Whether you enjoy the latest Hollywood blockbuster or you like to explore lesser-known ‘world cinema’ films, visit our Cinemas page for the options.

Sample our local food and drink

Enjoy a fantastic lunch or evening meal in one of our pubs and restaurants. Sample some locally-brewed ale and some locally-produced food on our seasonal menus. Whatever your taste in food, cause for celebration or budget, there are many restaurants and pubs waiting to welcome you in the Royal Borough of Windsor and Maidenhead. Browse our Food and Drink pages for all the options.

Want to discover more about what’s on?

See the list below or browse our What’s On pages for inspiration and use our ‘What’s On Search’ (above); we update windsor.gov.uk regularly with great event and what’s on ideas for the Windsor, Eton, Ascot and Maidenhead area.

We look forward to entertaining you.

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Number of results: 73

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Twinkle Twinkle

Maidenhead

It’s the longest night of the year and it’s hard to sleep. Gazing at the stars, surprising things start to happen… As the sun sets and the stars come out to shine, join the woodland animals as they gather together to celebrate the solstice.
Norden Farm Jazz Club: Marta Mathea Radwan and Friends - Christmas Special

Maidenhead

Award-winning conductor and vocalist Marta Mathea Radwan is joined by Alex Hutton (piano), Rob Rickenburg (bass) and Eric Ford (drums).
TripAdvisor Traveller Rating
2110 reviews
Jazzy Christmas at Danesfield with Rebecca Poole

Marlow on Thames

This December, celebrate the festive season in style with a Jazzy Christmas at Danesfield, a sparkling evening of live music with acclaimed singer-songwriter Rebecca Poole.
The Santa Show

Braywick Road, Maidenhead

It's Christmas Eve in the North Pole and the elves are making the final preparations to Santa’s sleigh before a crisis strikes! Will the children be able to help Santa save the day?
Windsor Jazz Club: Sarah Jane Eveleigh Quartet

Alma Road, Windsor

Sarah Jane Eveleigh is a passionate and gifted storyteller, praised for her interpretations of American Songbook standards, delivered with style, accuracy and class. Join us this evening for a Christmas-themed selection of jazz.
TripAdvisor Traveller Rating
255 reviews
The Albion Christmas Band

Maidenhead

The Albion Christmas Show is a seasonal mixture of carols, spoken word and humorous readings. It really is the perfect way to start your festivities.
Santa's Wondrous Workshop

Maidenhead

It’s a Christmas crisis! Santa’s Wondrous Workshop has run out of magic and stopped making toys. There’s only one way to fix it. Santa has sent for two of his favourite magicians to return magic to the North Pole and save Christmas!
Join The Magical…
TripAdvisor Traveller Rating
255 reviews
The Rymatones

Maidenhead

A high-energy Rock 'n' Roll band, inspired by the legends of the 1950s and 1960s. Bringing the music of Elvis Presley, Chuck Berry, Buddy Holly and more to life.
Red Hoax Chili Peppers

Windsor

The South of England's premier tribute act dedicated to celebrating the legendary sound and energy of the Red Hot Chili Peppers.
Syd Lawrence Orchestra: Diamond Big Band Show 60 Years

Windsor

The Syd Lawrence Orchestra, led by Chris Dean, celebrates 60 swinging years with a spectacular new show that brings the golden age of Big Band roaring into the future.
Dancing with the Stars Weekend

Old Windsor

Enjoy three days of spectacular dance showcases as your favourite TV stars perform up close and personal for a truly intimate experience unlike any other – learn to dance with the stars, see the costumes, plus hear all about their amazing journeys.
TripAdvisor Traveller Rating
1748 reviews
The King's Speech

Windsor

David Seidler’s The King’s Speech tells the remarkable story of Bertie, Duke of York, who must overcome a debilitating stammer in order to fulfil his destiny as King George VI. With the support of unconventional Australian speech therapist Lionel…
Fi.Fest

Maidenhead

Experience Fi.Fest: a feel good family-friendly summer music festival in Fifield, perfectly placed between Windsor and Maidenhead in Berkshire. Join us on 9 and 10 July for two days of live music, food and fun for all ages.