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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...Read More

Enjoy some arts and culture in Windsor and Maidenhead

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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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
1733 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.
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
TripAdvisor Traveller Rating
1731 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…
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…
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.
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.
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…
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).
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
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 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.
The Maidenhead Big Weekender

Maidenhead

Get ready for two unforgettable days of live music, delicious food, exciting entertainment and summer vibes as part of The Maidenhead Big Weekender.
Brazen Hodgepodge

Windsor

Brazen Hodgepodge is a sketch comedy show! A fast-paced evening of original sketch comedy scenes and songs. Whether it's current events or loathesome public figures, absurd situations or very familiar social problems, we will make fun of all of it.…
Half Term at Norden Farm

Maidenhead

Norden Farm Centre for the Arts is the place to keep the family entertained this May half term. With live shows and familiar characters - there’s plenty to choose from. Tickets for live shows are £13.50 | £11.50 under 16s | Family and Friends (4…
The Dumb Waiter by Harold Pinter

Windsor

Two Man Theatre Company—a newly formed duo with a passion for bold, character-driven storytelling. As a company, we're committed to exploring existing works through our own artistic lens, bringing fresh perspective and intent to every production.…
Cumberland Lodge Murder Mystery Weekend

Windsor

Step into the roaring twenties for a Murder Mystery weekend like no other. Join us this June for Cumberland Lodge's first-ever Murder Mystery Weekend, set in the glamorous world of 1924.
TripAdvisor Traveller Rating
252 reviews
Norden Farm Centre for the Arts

Maidenhead

Maidenhead’s only purpose built entertainment venue – offering gigs, comedy, films and more! With a licensed Café Bar for lunch, dinner or just drinks with friends.
TripAdvisor Traveller Rating
25 reviews
The Old Court

Windsor

The Old Court is a vibrant arts centre with an event programme that features an eclectic mix of live music, drama, comedy and film, and a bar run by Windsor & Eton Brewery.
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