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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: 51

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TripAdvisor Traveller Rating
1722 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.
TripAdvisor Traveller Rating
1722 reviews
Tours of Theatre Royal Windsor

Windsor

Peek behind the curtain at the historic Theatre Royal Windsor and discover over 240 years of theatrical history on a theatre tour.
TripAdvisor Traveller Rating
1722 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
1720 reviews
American Four Tops

Windsor

Direct from the USA, Soul Satisfaction’s American Four Tops show has been travelling all around the world, bringing all the sweet soul music and the Motown magic to their audiences.
TripAdvisor Traveller Rating
1720 reviews
The Comedy of Terrors!

Windsor

Rumpus Theatre Company presents the devilishly funny farce… The Comedy of Terrors! By John Goodrum.
TripAdvisor Traveller Rating
1720 reviews
The Manfreds – Maximum Rhythm ‘N’ Blues

Windsor

The Manfreds, featuring both former lead singers of Manfred Mann, Paul Jones and Mike d’Abo, will be recreating their fabulous Maximum Rhythm ‘N‘ Blues show for one night only at Theatre Royal Windsor!
TripAdvisor Traveller Rating
252 reviews
Mitch Benn – The Point

Maidenhead

Mitch Benn is a comedian, author, satirical songwriter, musician and actor. He is widely acknowledged as one of the best writers/performers of comedy songs in the UK. He is perhaps best known as the resident comic songwriter on BBC 4’s The Now Show…
TripAdvisor Traveller Rating
1722 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
1720 reviews
Country Superstars

Windsor

The world’s biggest country music tribute touring show – Dolly Parton and Friends Tribute Show – is coming to Theatre Royal Windsor with an award winning cast! This performance is a must-see for any fans of country music!
The Ripper Files!

Windsor

Rumpus Theatre Company present The Ripper Files, based on the world’s most famous case…
TripAdvisor Traveller Rating
1722 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…
TripAdvisor Traveller Rating
1722 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.
Hauntings

Maidenhead

A spellbinding evening of three tales of the supernatural from two of the world’s greatest writers of ghost stories: E F Benson and M R James.
TripAdvisor Traveller Rating
252 reviews
Hauntings

Maidenhead

A spellbinding evening of three tales of the supernatural told by actor Gerard Logan. Hauntings is at Norden Farm Centre for the Arts on Friday 20 December at 8pm. Tickets are £16 | £14 Supporters.
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…
Dancing with the Stars Weekend

Old Windsor

Spend the weekend with the stars of BBC Strictly Come Dancing at the stunning De Vere Beaumont Estate Hotel in Windsor.
Ed Byrne: Tragedy Plus Time

Maidenhead

Following a sell-out show last year, TV favourite Ed Byrne returns to Maidenhead with British Comedy Guide's No 1 Comedy show of 2023 and his most personal show to date.
Donaheys Learn to Dance in a Day Workshop

Reading

In Donahey's 4-hour weekend workshop you'll receive expert tuition in some of the world's most popular Ballroom and Latin dances.
Live Comedy in Windsor

Eton

Hey there, comedy lovers! Are you ready for an unforgettable night of laughter and fun? Full Frontal Comedy is proud to present some of the best award-winning comedians on the circuit!
A Christmas Carol

Windsor

WTG presents A Christmas Carol - A Ghost Story, Mark Gatiss’ thrilling adaptation of Charles Dickens' much-loved festive classic in an evening of spine-tingling suspense and joyful, musical delight.