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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: 38

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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!
(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…
TripAdvisor Traveller Rating
1732 reviews
The Dinosaur That Pooped A Rock Show

Windsor

Adapted from the number 1 best-selling books by Tom Fletcher and Dougie Poynter, the whole family will have a poopy good time at Theatre Royal Windsor, enjoying a brand new story for the stage. Featuring new songs by Tom and Dougie, a lot of laughs…
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
1732 reviews
One Night in Dublin

Windsor

The ultimate feel-good Irish music tribute show comes to Theatre Royal Windsor.
TripAdvisor Traveller Rating
1730 reviews
The Big Country Music Show

Windsor

It’s gonna be a sea of cowboy hats when The BIG Country Music Show rides into Windsor! From the award-winning band that brought you the hit touring production One Night in Dublin, this show has been wowing audiences and receiving outstanding reviews…
Puss in Boots

Windsor

Based on the original version by Charles Perrault, the Let's All Dance Ballet Company brings a new version of Puss in Boots about a friendship between a magical cat and a young man with a talent for music.
Little Shop of Horrors

Windsor

Come and join Windsor College Theatre Company down on Skid Row for the smash hit musical Little Shop of Horrors.
Spider's Web by Agatha Christie

Windsor

WTG presents Spider's Web by Agatha Christie - a conscious parody of the detective thriller, in which Christie delivers a unique blend of suspense and humour. There is tension and laughter in equal parts in an intricate plot of murder, police, drug…
Legally Blonde - The Musical

Windsor

Windsor College Theatre Company present the smash hit musical Legally Blonde. Music and Lyrics by Laurence O'Keefe and Nell Benjamin, Book by Heather Hach Based on the novel by Amanda Brown and the Metro-Goldwyn-Mayer motion picture
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.
Dancing with the Stars Weekend

Old Windsor

Spend the weekend with the stars of BBC Strictly Come Dancing at the stunning De Vere Beaumont Estate Hotel in Windsor.
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.
Stuart Henderson - Jazz Trumpet Greats! - Jazz Nights @ Frederick's

Maidenhead

Jazz Trumpet Greats! Stuart Henderson (http://stuarthendersontrumpet.co.uk/) has traversed the worlds of classical, military big band and jazz! For a good time as a member of the Scots Guards Band, he was the Queen’s trumpeter at all formal…
The Wedding Singer

Windsor

SWMTC Productions, the company who brought you the award-winning production of Shout! The Mod Musical and Sister Act present: The Wedding Singer.
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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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.…