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Entertainment

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: 27

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The Old Court Cinema: June Films

Windsor

Discover June film screenings at The Old Court Cinema, Windsor
The Old Court Cinema: May Films

Windsor

Discover May film screenings at The Old Court Cinema, Windsor
The Old Court Cinema: April Films

Windsor

Discover April film screenings at The Old Court Cinema, Windsor
The Old Court Cinema: July Films

Windsor

Discover July film screenings at The Old Court Cinema, Windsor
TripAdvisor Traveller Rating
1709 reviews
Filumena

Windsor

Felicity Kendal stars in Filumena, Eduardo de Filippo’s classic comedy (with English version by Keith Waterhouse & Willis Hall) set in the balmy heat of Naples that questions the family ties that bind us and whether we can ever escape our past.
Norden Farm: April/May films

Maidenhead

Journey around the world with Norden Farm’s spring Cinema line up.
TripAdvisor Traveller Rating
251 reviews
Jacob Hawley: SPACE

Maidenhead

Award-winning comedian comes to Norden Farm.
TripAdvisor Traveller Rating
251 reviews
Jonny and The Baptists: The Happiness Index / Ten Thankless Years

Maidenhead

A double bill of two shows in one night from cult multi-award winning musical-comedians Jonny and The Baptists.
TripAdvisor Traveller Rating
251 reviews
Rosie Holt: That’s Politainment!

Maidenhead

The worse the political career, the more lucrative the subsequent entertainment opportunities. Following a hugely successful Edinburgh Fringe season, Rosie takes this brand-new show on the road, to tightrope the thin line between politics and…
TripAdvisor Traveller Rating
251 reviews
St John’s Chamber Orchestra

Maidenhead

The Beethoven symphony cycle (21-25) continues with the titanic and stormy Fifth symphony. Chinese pianist Jianing Kong joins the St John’s Orchestra on piano.
TripAdvisor Traveller Rating
1709 reviews
Tours of Theatre Royal Windsor

Windsor

Peek behind the curtain at the historic Theatre Royal Windsor and discover over 240 years of theatrical history on a theatre tour.
TripAdvisor Traveller Rating
251 reviews
National Theatre Live: Nye

Maidenhead

Michael Sheen plays Nye Bevan in National Theatre Live: Nye, directed by Rufus Norris.
TripAdvisor Traveller Rating
251 reviews
The Lost Trades

Maidenhead

An evening of live folk and Americana music.
TripAdvisor Traveller Rating
251 reviews
Daliso Chaponda – Feed This Black Man Again

Maidenhead

Britain’s Got Talent star brings his comedy to Norden Farm.
TripAdvisor Traveller Rating
251 reviews
Martin Turner ex Wishbone Ash

Maidenhead

Martin Turner and his band celebrate the 50th anniversary of Wishbone Ash’s seminal double live album Live Dates.
TripAdvisor Traveller Rating
1709 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
251 reviews
Jessica Fostekew: Mettle

Maidenhead

Jessica Fostekew: Mettle. A brand new stand-up show about passion, pace and purpose.
TripAdvisor Traveller Rating
1709 reviews
Accolade

Windsor

Originally written and performed in 1950, Emlyn Williams’s Accolade is a dark and chilling look at the price of success, the power of trial-by-media, and remains a remarkably relevant play in the current age of ‘cancel culture’.
St George's Day Datchet Morris Dance-Out

Windsor

Datchet Morris will be dancing on Windsor Bridge on the evening of Tuesday 23 April from 20.00h to celebrate St George. We will be joined by Taeppas Tump, a ladies’ Morris side from Maidenhead.
TripAdvisor Traveller Rating
251 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.