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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.
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…
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
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…
TripAdvisor Traveller Rating
1731 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.
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.
St John’s Chamber Orchestra – Concert for Midsummer’s Day

Maidenhead

Join us for this special concert featuring two of the most popular of all concertos. St John’s Chamber Orchestra – Concert for Midsummer’s Day is at Norden Farm Centre for the Arts on Friday 21 June at 7.30pm. Tickets are £20.
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
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.
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
Shake It Up: The Improvised Shakespeare Show

Maidenhead

Shakespeare hasn’t written anything new for an age, so they thought they would give him a hand… Shake It Up: The Improvised Shakespeare Show is at Norden Farm Centre for the Arts on Thursday 26 June at 7.30pm. Tickets are £17.50. Age guidance 11+…
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!
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.
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
1733 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
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
1733 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.
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!
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.