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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 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 live music

Other Space Arts is a vibrant grassroots venue bringing together original live music, contemporary arts and plant-based food in the heart of Windsor. Housed in a beautifully-restored industrial space, just a short walk from the town centre, Other Space Arts offers a unique cultural experience for both locals and visitors.

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.

Enjoy some comedy

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.

Experience 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 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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Getting Triggy With It: Matt Parker does the Maths

Maidenhead

The stand up comedian and number one best-selling maths author returns to Maidenhead! Getting Triggy With It: Matt Parker does the Maths is at Norden Farm Centre for the Arts on Thursday 15 October at 8pm. Tickets are £26.50 | VIP Experience £76.50…
Krapp’s Last Tape

Maidenhead

Revel in Samuel Beckett’s riveting journey into the human soul. Krapp’s Last Tape is at Norden Farm Centre for the Arts on Friday 16 October at 7.30pm. Tickets are £20 (plus a £1.90 per transaction booking fee).
Day Glow: The Norden Farm Daytime Rave

Maidenhead

Remember when you could dance all night? Now you can - just earlier. This unique afternoon rave for grown ups is back by popular demand. Day Glow: The Norden Farm Daytime Rave is at Norden Farm Centre for the Arts on Saturday 17 October from 2pm -…
Dark Side of the Wall

Maidenhead

This award-winning Pink Floyd tribute band celebrate their heroes in well over two hours of spectacular live music and visual effects - Dark Side of the Wall is at Norden Farm Centre for the Arts on Saturday 17 October at 8pm. Tickets are £24.50…
UZ MI LIVE

Vansittart Estate, Windsor

UZ MI Records presents UZ MI LIVE A Night of Underground Live Electronic Music, spotlighting the unique live performances of a carefully selected artist and DJs. Join us in October for an unforgettable experience in the heart of Berkshires…
Windsor Jazz Club: Monkin' Around Trio

Alma Road, Windsor

Here are three friends getting together to pay homage to one of the greatest Jazz composers of the 20th century, Thelonious Monk.
TripAdvisor Traveller Rating
1748 reviews
The Turn of the Screw

Windsor

A masterwork of psychological suspense and the inspiration for Susan Hill’s The Woman in Black, Henry James’ classic novella The Turn of the Screw is brought to life in this brand-new stage adaptation by Olivier Award-winning playwright Morgan Lloyd…
Jazz Jam for players

Alma Road, Windsor

A round circle jam where you get to play all night, and solo on every song. With no audience present, you're free to practise, experiment and develop your style
Norden Farm Jazz Club: Dave Barry’s Fourcast Featuring Dave O’Higgins

Maidenhead

An all star line-up head to the Studio for Norden Farm Jazz Club: Dave Barry’s Fourcast Featuring Dave O’Higgins at Norden Farm Centre for the Arts on Friday 23 October at 8pm. Tickets are £17.50 (plus a £1.90 per transaction booking fee).
A Feast of the 40s

Holyport, Maidenhead

Maidenhead Musical Comedy Society presents "A Feast of the 40s", a heart-warming musical set in the wartime years, filled with humour, charm and unforgettable songs from the era
Sherwood Roberts Live

Windsor

Sherwood Roberts returns to his local venue celebrating the release of his third album, Connection to Identity.
Young Musician Evening with Samrat Majumder

Windsor

Cumberland Lodge are hosting an evening with a very talented young musician, guitarist Samrat Majumder from the Young Classical Artists Trust. Samrat is a Scottish-Indian classical guitarist who is an ambassador for the Royal Conservatoire of…
TripAdvisor Traveller Rating
1748 reviews
The Snow Queen

Windsor

Following the success of their charming productions of A Christmas Carol last autumn and The Nutcracker in 2024, Ballet Theatre UK is delighted to return to Windsor this autumn half-term with The Snow Queen: a magical re-telling of Hans Christian…
Luca Silvestrini’s The Magic Flute

Maidenhead

A bold and playful retelling, inspired by Mozart’s beloved opera - Luca Silvestrini’s The Magic Flute is at Norden Farm Centre for the Arts on Tuesday 27 October at 5pm. Tickets are £13.50 | £11.50 under 16s | £45 Family and Friends (4 people), plus…
The Vinyl Frontier - Autumn Season

Maidenhead

Host Jeff Lloyd returns with a brand-new season of monthly vinyl music events this Autumn at Norden Farm Centre for the Arts. Tickets are £13.50 (plus a £1.90 per transaction booking fee).
TripAdvisor Traveller Rating
1748 reviews
A Man For All Seasons

Windsor

Direct from the West End, the greatest, most powerful and dangerous figures who shaped English history are brought vividly to life in Robert Bolt’s award-winning play.
Windsor Jazz Club: Eriko Ishihara Trio

Alma Road, Windsor

A fine singer and an excellent jazz pianist Eriko has established an enviable reputation on the UK jazz scene, working at the likes of Ronnie Scott's, 606 Club and the Royal Festival Hall, as well as major concert halls in Hong Kong and Korea.
TripAdvisor Traveller Rating
1748 reviews
Jack And The Beanstalk

Windsor

Climb into a world of magic, mischief, and massive fun as Theatre Royal Windsor proudly presents Jack And The Beanstalk, the giant of all pantomimes!
George Michael Tribute night

Maidenhead

Join us for an incredible evening of music, dining, and entertainment at our George Michael Tribute Party Night – a celebration of one of pop’s most iconic artists.
Absolute U2

Windsor

Absolute U2 brings together seasoned musicians, veterans of hundreds of live shows, united by one mission: to recreate the sound, spirit, and electric energy that made U2 legends.