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Theatre Royal, A Christmas Carol (photo credit: Simon Vail)

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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 some 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 some live music

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.

Smokey Joe’s Roadhouse is a live music venue located right in the middle of Maidenhead’s town centre.

Watch something funny

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.

Enjoy 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 some of 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: 46

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TripAdvisor Traveller Rating
506 reviews
Christmas Carols in The Savill Garden Visitor Centre

Englefield Green

Relax in The Savill Garden Kitchen as you surround yourself with festive music and carols in The Savill Garden Visitor Centre, performed by local groups and choirs.
The Old Court Cinema

Windsor

Discover film screenings at The Old Court Cinema, Windsor. With its big screen, immersive Dolby surround sound and comfortable seating, the Old Court’s cinema in Windsor is your local big screen experience and the perfect place to enjoy a wide…
Blood Brothers

Windsor

Written by Willy Russell, the legendary Blood Brothers tells the captivating and moving tale of twins who, separated at birth, grow up on opposite sides of the tracks, only to meet again with fateful consequences.
TripAdvisor Traveller Rating
1725 reviews
Boys from The Blackstuff

Windsor

James Graham‘s powerful new adaptation of Alan Bleasdale’s BAFTA award-winning TV series, directed by Kate Wasserberg, starts its 2025 national tour in Windsor, direct from the National Theatre and West End.
TripAdvisor Traveller Rating
1723 reviews
Mane Chance Comedy Night

Windsor

Theatre Royal Windsor is proud to host the return of the Mane Chance Comedy Night.
Far from the Madding Crowd

Windsor

Thomas Hardy’s masterpiece about love, class and gender roles is set against the rural landscape of Victorian England and is thrillingly brought to life in a new adaptation by the acclaimed Conn Artists Theatre Company, performed by an ensemble cast…
TripAdvisor Traveller Rating
1723 reviews
Beyond the Barricade

Windsor

Beyond the Barricade, the UK’s longest running musical theatre concert tour, is back for 2025. Join the cast at Theatre Royal Windsor for two hours of the best of Broadway and the West End, featuring the songs that have made audiences return over…
TripAdvisor Traveller Rating
1723 reviews
Cinderella

Windsor

Get ready to be whisked away to a world of magic, mischief and make-believe! Theatre Royal Windsor proudly presents the spectacular pantomime, Cinderella, for the winter 25/26 season.
TripAdvisor Traveller Rating
1725 reviews
Cirque – The Greatest Show, Reimagined

Windsor

Cirque – The Greatest Show has been Reimagined and is back for 2025 – bigger, bolder, and more electrifying than ever! Get ready for a dazzling fusion of musical theatre and jaw-dropping circus acts, taking the original circus-meets-musical-theatre…
TripAdvisor Traveller Rating
1723 reviews
The Comedy of Terrors!

Windsor

Rumpus Theatre Company presents the devilishly funny farce… The Comedy of Terrors! By John Goodrum.
TripAdvisor Traveller Rating
1725 reviews
Disco Inferno

Windsor

Let’s dance, let’s shout, come and shake your body down with the electrifying show that screams glitter balls and good times all the way! Book now for this all-singing, all-dancing celebration of everything D.I.S.C.O.
TripAdvisor Traveller Rating
1725 reviews
Pride and Prejudice* (*Sort Of)

Windsor

Following its triumphant triumphs in the West End, where it won the Olivier Award for Best Comedy and the Evening Standard Award, Pride and Prejudice* (*Sort Of) is a unique and audacious retelling of Jane Austen’s most iconic love story.
Sophie Duker: But Daddy, I Love Her (warm up show)

Maidenhead

Sophie Duker is back and warming up her show before she heads out on tour! Sophie Duker: But Daddy, I Love Her (warm up show) is at Norden Farm Centre for the Arts on Wednesday 15 January at 8pm. Tickets are £14.
TripAdvisor Traveller Rating
1725 reviews
Theatre Royal Windsor

Windsor

The Theatre Royal Windsor is a beautiful Edwardian theatre nestling between Windsor Castle and the River Thames and is the only unsubsidised producing theatre to operate all year round in Britain.
TripAdvisor Traveller Rating
252 reviews
Pop-Up Bowie

Maidenhead

Experience the magic of Bowie’s music live with thrilling artistry, a theatrical performance that honours the revolutionary icon himself in the most respectful of ways.
Just Between Ourselves

Windsor

In perhaps his most emotionally charged play, Alan Ayckbourn masterfully evokes a world of hidden tensions and suppressed hostility. He skillfully navigates the tightrope between comedy and tragedy, guiding us towards a hilarious, yet chilling…
TripAdvisor Traveller Rating
1725 reviews
Dial M for Mayhem

Windsor

Middle Ground Theatre Company Ltd is delighted to present the world stage premiere of Dial M For Mayhem, a brand new charming farcical comedy drama from the author and director of the hugely successful courtroom phenomenon The Verdict.
TripAdvisor Traveller Rating
252 reviews
The Royal Ballet: The Nutcracker

Maidenhead

Discover the enchantment of ballet with this sparkling festive treat for the whole family.
The Ripper Files!

Windsor

Rumpus Theatre Company present The Ripper Files, based on the world’s most famous case…
TripAdvisor Traveller Rating
1725 reviews
Dick Whittington

Windsor

Expect traditional pantomime comedy capers, dazzling dancers, colourful costumes and a sprinkling of Magic as we join Dick Whittington to see if the streets of London really are paved with gold…