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

Follow Us...

La Bouche Manouche featuring Irene Serra

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: 41

, 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
1732 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.
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
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.
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
1732 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.
You Choose

Maidenhead

Based on the brilliant book by Pippa Goodhart and Nick Sharratt, every show is unique! You Choose is at Norden Farm Centre for the Arts on Thursday 29 May at 11.30am and 2pm. Tickets are £13.50 | £11.50 under 16s | £45 Family and Friends (4 people).
TripAdvisor Traveller Rating
1730 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 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
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
252 reviews
St John’s Chamber Orchestra

Maidenhead

Prize winning Hong Kong pianist Alex Wun appears at Norden Farm Centre for the Arts. St John’s Chamber Orchestra perform on Saturday 10 May at 7.30pm. Tickets are £21.50 | under 18s free.
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.
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…
TripAdvisor Traveller Rating
1730 reviews
One Night in Dublin

Windsor

The ultimate feel-good Irish music tribute show comes to Theatre Royal Windsor.
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.
TripAdvisor Traveller Rating
1730 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.
Sorrel Nation

Maidenhead

Travelling troubadour brings a soulful mix of folk-rock and country. Sorrel Nation performs at Norden Farm Centre for the Arts on Friday 16 May at 7.30pm. Tickets are £16.
TripAdvisor Traveller Rating
1732 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.
(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…
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,…