To provide you with the best experience, cookies are used on this site. Find out more here.

Follow Us...

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

You are here: Home > Things to Do > Entertainment

Accommodation
Search
Things to Do
Search
What's On
Search
Food & Drink
Search
Shopping
Search

Accommodation Search

Things to Do Search

What's On Search

Food & Drink Search

Shopping Search

Accommodation Search

Things to Do Search

What's On Search

Food & Drink Search

Shopping Search

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.

Number of results:

Number of results: 33

, currently showing 1 to 20.

Sort By: A-Z Lowest A-Z Highest

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
1729 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
1729 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
1731 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
1731 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
1731 reviews
The Comedy of Terrors!

Windsor

Rumpus Theatre Company presents the devilishly funny farce… The Comedy of Terrors! By John Goodrum.
TripAdvisor Traveller Rating
1729 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
1731 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
1729 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
1729 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
1729 reviews
Mane Chance Comedy Night

Windsor

Theatre Royal Windsor is proud to host the return of the Mane Chance Comedy Night.
TripAdvisor Traveller Rating
1729 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
Oh la la! Quintet – A Night in Paris

Maidenhead

Paris comes to Maidenhead for one night only. Oh la la! Quintet mix Parisian folk music (musette), impressionist music, French chanson with unforgettable 20s upbeat and 50s smooth jazz.
TripAdvisor Traveller Rating
1731 reviews
The Showstoppers’ Kids Show

Windsor

The Showstoppers’ Kids Show is an improvised musical show for kids of all ages, from Olivier Award-winning West End improvisers, The Showstoppers.
TripAdvisor Traveller Rating
1731 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.
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…
The Ripper Files!

Windsor

Rumpus Theatre Company present The Ripper Files, based on the world’s most famous case…
Screenings direct from The Royal Opera House at Norden Farm

Maidenhead

The Royal Ballet and Opera in Covent Garden is the at the heart of London and British cultural life. The 2024/25 cinema season brings exciting new productions to the screen at Norden Farm Centre for the Arts. They will be showing between January and…
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
1731 reviews
Cruel Intentions, the '90s musical

Windsor

Following sell-out seasons in London and New York, the brand new smash hit musical Cruel Intentions is coming to Theatre Royal Windsor! Based on the iconic film and inspired by Les Liaisons Dangereuses, it’s packed with ’90s pop classics.