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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: 43

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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…
TripAdvisor Traveller Rating
1732 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
1730 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
1730 reviews
One Night in Dublin

Windsor

The ultimate feel-good Irish music tribute show comes to Theatre Royal Windsor.
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
1730 reviews
The Dreamer

Windsor

Visit Theatre Royal Windsor for a brand new magic show for 2025! Star of The Greatest Magician™, and the BBC’s most broadcast magician of the last decade, the award-winning James Phelan debuts this breath-taking new magic show.
TripAdvisor Traveller Rating
1732 reviews
Go Your Own Way – A Tribute to Fleetwood Mac

Windsor

Go Your Own Way is the spellbinding show featuring music from the legendary multiple Grammy Award-winning Fleetwood Mac.
TripAdvisor Traveller Rating
1732 reviews
The Enormous Crocodile

Windsor

This august The Enormous Crocodile is weaving his way through the jungle to Theatre Royal Windsor in search of delicious little fingers and squidgy podgy knees…Only the other jungle creatures can foil his secret plans and clever tricks, but they’re…
TripAdvisor Traveller Rating
1730 reviews
Fireman Sam Live! The Great Camping Adventure

Windsor

Norman wants to go on an adventure to impress his friends, so when two famous animal explorers arrive in Pontypandy, he decides to follow them into the mountains.
TripAdvisor Traveller Rating
1730 reviews
The Magic of Motown

Windsor

Seen by millions, The Magic of Motown is back with its 20th Anniversary Tour! Come celebrate at Theatre Royal Windsor as we Reach Out and show you there Ain’t No Mountain High Enough with the biggest Motown party of the year.
TripAdvisor Traveller Rating
1732 reviews
The Dusty Show

Windsor

The Dusty Show is the ultimate celebration of a true British pop icon. Join us at the Theatre Royal Windsor for an unforgettable evening of wall-to-wall hits and classics spanning the success of Dusty Springfield’s life and music starring…
TripAdvisor Traveller Rating
1732 reviews
Sara Pascoe: A Night of Outside the Box Comedy Club

Windsor

Outside the Box Comedy Club returns to Theatre Royal Windsor with headliner Sara Pascoe! Sara will be supported on the night by some top comedians.
TripAdvisor Traveller Rating
1732 reviews
UK Pink Floyd Experience

Windsor

Celebrating 50 years since the release of the ‘Wish You Were Here’ album, UK Pink Floyd Experience recreates the atmosphere of Floyd live – featuring top-flight musicians, a stunning light show and more than two hours of incredible music.
TripAdvisor Traveller Rating
1730 reviews
Arrival – The Hits of ABBA

Windsor

Calling all Dancing Queens – get ready to embark on a musical journey back to the 70s where disco reigned supreme and ABBA ruled the charts! Arrival – The Hits of ABBA’s multi award-winning show is returning in 2025 following sell out shows in more…
TripAdvisor Traveller Rating
1730 reviews
Mane Chance Comedy Night

Windsor

Theatre Royal Windsor is proud to host the return of the Mane Chance Comedy Night. Join us for an evening that will leave you in peals of laughter!
TripAdvisor Traveller Rating
1732 reviews
Showstopper! The Improvised Musical

Windsor

Showstopper! The Improvised Musical is coming to Theatre Royal Windsor, promising spontaneous musical comedy at its absolute finest, direct from the West End!
TripAdvisor Traveller Rating
1730 reviews
The Dinosaur That Pooped A Rock Show

Windsor

Adapted from the number 1 best-selling books by Tom Fletcher and Dougie Poynter, the whole family will have a poopy good time at Theatre Royal Windsor, enjoying a brand new story for the stage. Featuring new songs by Tom and Dougie, a lot of laughs…
TripAdvisor Traveller Rating
252 reviews
Romeo and Juliet

Maidenhead

Two households, both alike in dignity. In broken Belfast, where we lay our scene… A new version of Romeo and Juliet is at Norden Farm Centre for the Arts on Thursday 6 March at 8pm. Tickets are £16 | £14 Supporters. Age guidance 11+ years.
TripAdvisor Traveller Rating
1732 reviews
Science Museum Live

Windsor

The Science Museum is coming to Windsor! Experience the brand-new stage show from Mark Thompson Productions which will ignite your curiosity, fuel your imagination and inspire you in new and exciting ways.
TripAdvisor Traveller Rating
1730 reviews
The Big Country Music Show

Windsor

It’s gonna be a sea of cowboy hats when The BIG Country Music Show rides into Windsor! From the award-winning band that brought you the hit touring production One Night in Dublin, this show has been wowing audiences and receiving outstanding reviews…