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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 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

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.

In Windsor we have a thriving Theatre Royal, a beautiful Edwardian theatre nestling in the shadow of Windsor Castle offering a wide range of live shows and the ever-popular annual pantomime! 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 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 come to Windsor and Maidenhead, including 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. 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
250 reviews
Helen Bauer: Grand Supreme Darling Princess

Maidenhead

Helen Bauer brings a show all about the women in her life, from her mother to her best friend, and that one girl who was mean in 2008. And Disney Princesses.
The Old Court Cinema: September Films

Windsor

Discover September film screenings at The Old Court Cinema, Windsor
The Old Court Cinema: October Films

Windsor

Discover October film screenings at The Old Court Cinema, Windsor
TripAdvisor Traveller Rating
250 reviews
Draining The Swamp

Maidenhead

Meet Sir Oswald and Lady Diana Mosley and discover the private personas behind the Fascist leader and his unorthodox wife. A story about politics and fascism is told on stage.
Aladdin

Windsor

Make your wishes come true and join us on this magical carpet ride of adventure and fun. Featuring Theatre Royal Windsor’s traditional pantomime comedy capers, with a sprinkle of magic, dazzling dancers, colourful costumes and a glittering star…
Dire Streets

Maidenhead

The classic songs of one of the world’s greatest guitar bands is brought back to life. Dire Streets is at Norden Farm Centre for the Arts on Saturday 7 October.
The Windsor Fringe

Windsor

We are very excited to present an eclectic programme of shows and events, in collaboration with local arts groups and venues. We hope you enjoy our Mini Fringe!
The Upbeat Beatles

Maidenhead

Performing to sell out venues for over 20 years, paying homage to the greatest band in history. The Upbeat Beatles are at Norden Farm Centre for the Arts on Friday 29 September.
TripAdvisor Traveller Rating
1699 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.
Norden Farm: September films

Maidenhead

Latest film screenings – Barbenheimer heads to the Farm. The cinema screen at Norden Farm Centre for the Arts showcases the latest blockbuster, family, arthouse and event cinema films. Films are £10.50 | £9.50 conc. Bring Baby screenings are £5.50…
Gameplan

Windsor

Theatre Royal Windsor is thrilled to welcome back the Paul Taylor-Mills’ Sidmouth Rep company for this classic comedy drama. Teenage Sorrel fights to keep herself and her abandoned mother, once a dot.com businesswoman, financially afloat by setting…
Flatspin

Windsor

Theatre Royal Windsor is thrilled to welcome back the Paul Taylor-Mills’ Sidmouth Rep company for this classic comedy thriller. Purchase tickets for 2 shows in the Damsels in Distress trilogy and get the 3rd show free!*
Wilson & Wakeman Tour 2024

Windsor

Damian Wilson is an English songwriter and vocalist who’s known for his exploration into different genres and is considered one of the most versatile singers in rock. To this day he has released 6 solo albums and 3 albums as a duo with Adam Wakeman.
The Chicago Blues Brothers

Windsor

The Chicago Blues Brothers have put the band back together and are ‘Cruisin for a Bluesin’ taking you to the music capitals of the USA for one night of spectacular live music. This award-winning show is bringing you the very best in Rhythm and…
Kevin Cruise's Halloween Spooktacular

Windsor

Join Kevin for a full spooktacular family show and after show disco just like in the old days! A show full of dancers, competitions, game shows, and a very special spooky guest!
Heathers The Musical

Windsor

Winner of the WhatsOnStage award for BEST NEW MUSICAL! Due to overwhelming demand and following three smash hit London seasons and a national tour, Heathers the Musical returns to Windsor to conclude its tour!
The Tennessee Country Christmas Show

Windsor

For The first time ever a ‘Tennessee Country Christmas’ is coming to Celebrate the festive Season here in the UK!
A Tennessee Christmas celebrates renditions of Christmas favourites in a Country Style combined with some of the biggest selling hits…
12 Angry Men

Windsor

Following a record-breaking West End season, this powerful production of TWELVE ANGRY MEN is back in session! Reginald Rose’s gripping courtroom thriller has been hailed as the ‘classiest, most intelligent drama in the West End’. It brings the…
Johnny Cash Roadshow

Windsor

The only show to be endorsed by the Cash Family!
The Johnny Cash Roadshow is back on top form for 2023 with a brand new show. This year, award winning Clive John pays homage to Cash’s American Recordings alongside his iconic Wife, June Carter,…
TripAdvisor Traveller Rating
250 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.