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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! Read on for some of our top entertainment tips that we hope will keep you most amused.

Please contact individual attractions for the latest opening arrangements as restrictions are lifted. There will be new ways of doing things, at least for a little while.

Enjoy some arts and culture in Windsor and Maidenhead

We have two lively arts centres – Norden Farm and the Old Court – offering a whole host of great events including comedy, theatre, film and music.

In Windsor we have a thriving Theatre Royal. 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 spaces 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 and the Old Court 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 have come to Windsor and Maidenhead, such as Greg Davies, 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.

Enjoy 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?

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: 16

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TripAdvisor Traveller Rating
243 reviews
Kipper's Snowy Day

Maidenhead

It's snowing! And Kipper is very excited. Kipper and his friend Tiger go on an adventure in the snow – but can they find their way home? Book now for Norden Farm's Christmas show...
The Little Prince

Maidenhead

Add some magic to your October half term with the award winning The Little Prince. The family show is at Norden Farm Centre for the Arts from Wednesday 27 October – Saturday 30 October at 11.30am and 3.30pm. Tickets are £12 | £10 under 16s | Family…
The Platinum Jubilee Celebration - A Gallop Through History

Windsor

The Platinum Jubilee Celebration will see over 500 horses and 1,000 performers create a 90 minute piece of spellbinding arena theatre that will include actors and artists, musicians, international military displays from the Commonwealth and Europe,…
The Cherry Orchard

Windsor

Ranevskya returns following a five-year absence to discover her estate, including her beloved cherry orchard, are to be auctioned off to pay debts accrued by the family in Chekhov’s theatrical masterpiece. Francesca Annis stars as Ranevskya, Ian…
Hundred Watt Club - A Halloween evening of burlesque

Maidenhead

Hundred Watt Club invite you to peek inside their cabinet of curiosities and celebrate Halloween with an evening of bizarre burlesque, queer cabaret and sublime circus entertainment.
TripAdvisor Traveller Rating
1665 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
19 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.
Stand up Comedy with Stuart Laws

Windsor, UK

Join stand up and Old Court regular Stuart Laws (Amazon Prime, BBC) for a night of stand up comedy with some of the best comedians in the country.
Luke Wright, The Ballad Seller

Windsor

Come down to Windsor Library for our ever first Comedy Night. Join us and enjoy comedian Luke Wright entertaining us with stories for the modern ear. ‘Expect scandal, excess, and beautiful flawed humanity...’
All Together Now!

Windsor

A fantastic celebration of musical theatre, this bespoke show is being performed all over the globe on the same weekend, with favourites from shows we've already done such as 'Tomorrow' from Annie and 'We're all in this together' from High School…
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.
An Evening with Anton Du Beke & Erin Boag

Old Windsor

Spend the evening with Strictly Come Dancing Stars Anton Du Beke & Erin Boag. Enjoy a fabulous evening as the Strictly stars perform. Learn to dance with them, plus hear all about their Strictly journeys.
Carl Orff: Carmina Burana - RFS, WMSO, MCS, DMSCC

Braywick Road, Maidenhead

ROYAL FREE SINGERS and WINDSOR & MAIDENHEAD SYMPHONY ORCHESTRA | With Maidenhead Choral Society and Dedworth Middle School Children’s Choir
Aidan Goatley: The 12 Films of Christmas

Windsor

Deck the halls and grab the popcorn as comedian Aidan Goatley shouts 'action' on a brand-new show of cinematic based niceness that will warm your heart, no matter the weather.
TripAdvisor Traveller Rating
243 reviews
Norden Farm Centre for the Arts

Maidenhead

Maidenhead’s only professional arts and entertainment venue – with gigs, comedy, film, theatre, gallery, classes and cafe bar. We offer a wide range of high quality artistic events and participatory opportunities for the whole community.
Forever Yours, Casanova

Windsor

A humorous romp of mistaken identities, dastardly plots, revenge and a relentless cardinal bent on the destruction of the scandalous Casanova! The year is 1770 and this chapter of the infamous lover's story runs deep with deception, passion,…