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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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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…
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.
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.
Kate Cheka - A Messiah Comes

Maidenhead

After a sellout at the 2024 Edinburgh Fringe Festival, this award nominated show comes to Maidenhead. Kate Cheka - A Messiah Comes is at Norden Farm Centre for the Arts on Friday 30 May at 8pm. Tickets are £16.50.
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!
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.
Firelight Trio

Maidenhead

Playing European music that is evocative, inventive and endlessly exciting. Firelight Trio perform at Norden Farm Centre for the Arts on Thursday 12 June at 8pm. Tickets are £16.50.
(This Is Not A) Happy Room

Windsor

Meet the Hendersons; a happily dysfunctional family, coming together for their dad’s third (or fourth?) wedding. But nobody expects the death of his bachelorhood to become an actual funeral…Surely it would be a waste of the hotel's function room not…
Michael Akadiri – Trust Me, I’m a Daddy

Maidenhead

Multi-award-winning comedian and junior doctor brings us his sophomore show. Michael Akadiri – Trust Me, I’m a Daddy is at Norden Farm Centre for the Arts on Saturday 17 May at 8pm. Tickets are £16.50 | £15 NHS
The Simon Spillett Quartet

Maidenhead

A musician who has worn many hats in jazz over his twenty five year career. The Simon Spillett Quartet is at Norden Farm Centre for the Arts on Friday 23 May at 8pm. Tickets are £17.50.
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
252 reviews
April and May Cinema Screenings at Norden Farm

Maidenhead

Norden Farm Centre for the Arts in Maidenhead have announced their latest cinema line up – and there’s something for everyone heading to their screen this April and May.
Tomorrow Bird

Maidenhead

Think The Civil Wars meets Simon and Garfunkel. Tomorrow Bird are at Norden Farm Centre for the Arts on Saturday 24 May at 8pm. Tickets are £15.50
Gasper Nali

Maidenhead

This not-so-traditional babatoni player is from the small town of Nkhata Bay on the shore of Lake Malawi. Gasper Nali is at Norden Farm Centre for the Arts on Thursday 29 May at 8pm. Tickets are £17.50.
TripAdvisor Traveller Rating
1730 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.
The Great Big Dinosaur Show

Maidenhead

Which dinosaur had teeth as big as a banana? Which dinosaur weighed the same as 10,000 cats? The Great Big Dinosaur Show is at Norden Farm Centre for the Arts on Wednesday 28 May at 11.30am and 2pm. Tickets are £13.50 | £11.50 under 16s | Family and…
TripAdvisor Traveller Rating
1730 reviews
One Night in Dublin

Windsor

The ultimate feel-good Irish music tribute show comes to Theatre Royal Windsor.
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…
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.
Lenny Henry: Work in Progress

Maidenhead

He’s taking to the standup stage once again. Lenny Henry: Work in Progress is at Norden Farm Centre for the Arts on Tuesday 27 May at 8pm [SOLD OUT], Wednesday 28 May at 8pm [SOLD OUT] and Thursday 29 May at 12pm. Tickets are £19.50. Age guidance…