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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: 34

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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
1731 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
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…
Jaz Delorean

Maidenhead

He has a colourful past together with a wild and wandering present. Jaz Delorean performs at Norden Farm Centre for the Arts on Friday 6 June at 8pm. Tickets are £19.
Surinderella

Windsor

Surinderella is a spectacular all-singing, all-dancing tale set in the Bolly-Woods, where the naach is non-stop, the drama is bigger than your aunties’, and the romance is straight out of a filmi blockbuster!
TripAdvisor Traveller Rating
1733 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
Twist & Shout

Windsor

An all-star cast from the West End deliver a musical powerhouse of a show at Theatre Royal Windsor. It starts with the explosion of Brit Pop in 1962 through to the era of Flower Power and Free Love of the late Sixties.
James Church’s Cabaret Night with Cassidy Janson

Maidenhead

An evening with Olivier award-winning actress. James Church’s Cabaret Night with Cassidy Janson is at Norden Farm Centre for the Arts on Saturday 7 June at 8pm. Tickets are £25.50.
TripAdvisor Traveller Rating
1731 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
1731 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
1731 reviews
The Bon Jovi Experience

Windsor

Immerse yourself in a phenomenal celebration of Bon Jovi’s timeless classics as the official band to Bon Jovi recreates the magic that defined an era with electrifying energy – transporting you back to the heyday of stadium rock.
Rebeca Ortega Flamenco – Silences

Maidenhead

This dance performance is theatrically woven together. Rebeca Ortega Flamenco – Silences is at Norden Farm Centre for the Arts on Friday 27 June at 8pm. Tickets are £18.
TripAdvisor Traveller Rating
1731 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…
Live at the Bandstand

Windsor

Come and enjoy live band performances in the open air this summer. Windsor and Eton Business Partnership presents Windsor’s Live at the Bandstand programme 2025.
Windsor and Eton Living Advent Calendar

Windsor and Eton

Enjoy a different 15-minute live performance every evening of Advent with the Windsor and Eton Living Advent Calendar. Performances will range from songs, carols, music, poetry, book excerpts, creative arts, notes from local history or folklore,…
Raul Kohli – Raul Brittania

Maidenhead

Award-winning comedian and proud Brit. Raul Kohli – Raul Brittania is at Norden Farm Centre for the Arts on Thursday 19 June at 8pm. Tickets are £15.50.
Elvis Returns

Maidenhead

Get ready for an unforgettable evening as the UK’s most exciting Elvis tribute band hits the stage this Independence Day! Elvis Returns performs at Norden Farm Centre for the Arts on Friday 4 July at 8pm. Tickets are £25.
TripAdvisor Traveller Rating
1733 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
1733 reviews
One Night in Dublin

Windsor

The ultimate feel-good Irish music tribute show comes to Theatre Royal Windsor.
Avalon Edinburgh Preview: Pierre Novellie and Toussaint Douglas

Maidenhead

A double header of comedy as two top comedians warm up ahead of the Edinburgh Festival. Avalon Edinburgh Preview: Pierre Novellie and Toussaint Douglas are at Norden Farm Centre for the Arts on Thursday 5 June at 8pm. Tickets are £13.50.