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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

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.

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: 48

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TripAdvisor Traveller Rating
1735 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.
Other Space Arts

Windsor

Other Space Arts (OSA) is a grassroots live music and arts venue with a plant-based café, restaurant and bar, open Thursday to Sunday. Located just a short walk from Windsor town centre, OSA hosts original performances, live music and DJs in a…
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.
External Links
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The Old Court Cinema

Windsor

Discover film screenings at The Old Court Cinema, Windsor. With its big screen, immersive Dolby surround sound and comfortable seating, the Old Court’s cinema in Windsor is your local big screen experience and the perfect place to enjoy a wide…
The Windsor Fringe

Windsor

Windsor Fringe is the second oldest fringe in the UK after Edinburgh, and showcases an innovative and affordable programme of music, dance, comedy, drama, art and more!
The Great Big Community Show

Maidenhead

As part of their 25th anniversary celebrations, Norden Farm presents The Great Big Community Show on Saturday 20 September at 8pm. Tickets are £10.
TripAdvisor Traveller Rating
1733 reviews
The Signalman

Windsor

Middle Ground Theatre Company Ltd is delighted to announce a new extended adaptation of their hugely successful production of Charles Dickens’ nerve-tingling masterpiece The Signalman.
Hansel & Gretel the Ballet

Windsor

The Let's All Dance ballet company presents this captivating new ballet, adapted from the original Brothers Grimm fairytale.
TripAdvisor Traveller Rating
1733 reviews
Michael, The Magic of Michael Jackson

Windsor

Take a journey back in time to remember Michael Jackson – the man, the music and the magic. The show features a live band, dazzling costumes and the performer’s iconic dance routines. It also showcases the greatest hits of Michael Jackson and also…
TripAdvisor Traveller Rating
1735 reviews
The Void

Windsor

The Void is an original story inspired by iconic horror films Alien and The Thing, produced by Thunder Road and Watford Palace. Don’t miss out on this terrifying new theatrical event in the run up to Halloween!
Impromptu Shakespeare

Maidenhead

Hold onto your doubles, ruffs and trunk hose. The Bard is back! Impromptu Shakespeare is at Norden Farm Centre for the Arts in Maidenhead on Wednesday 1 October at 7.30pm. Tickets are £19.50. Age guidance 12+ years.
Matt Richardson - Brash

Maidenhead

Multi award-winning stand up Matt Richardson returns to Norden Farm Centre for the Arts with his latest show Brash on Thursday 2 October at 8pm. Tickets are £16.
Joe Wells - Daddy Autism

Maidenhead

Critically acclaimed comedian Joe Wells explores fatherhood through the lens of neurodiversity in his new show Daddy Autism at Norden Farm Centre for the Arts on Friday 3 October at 8pm. Tickets are £16.50.
TripAdvisor Traveller Rating
1733 reviews
Locomotive For Murder – The Improvised Whodunnit

Windsor

Pinch Punch welcome you aboard Locomotive for Murder: The Improvised Whodunnit, a totally improvised, totally hilarious murder mystery where killing the cast and cracking the case is in your hands. Expect shaky alibis and silver-tongued sleuths…
Martin Turner ex Wishbone Ash

Maidenhead

Martin Turner ex Wishbone Ash return to the stage at Norden Farm Centre for the Arts on Friday 3 October at 8pm. Tickets are £23.50.
the next act: Fringe Theatre Festival

Vansittart Trading Estate, Windsor

A day-long festival of Fringe Theatre shows from around the country.
Rachael McShane and the Cartographers

Maidenhead

Prepare for a powerful blend of traditional folk and contemporary sounds as Rachael McShane and the Cartographers head to Norden Farm Centre for the Arts in Maidenhead on Saturday 4 October at 8pm. Tickets are £15.
A Night at the Opera at the Windsor Guildhall

Windsor

Join us in the historic Council Chamber at Windsor Guildhall, surrounded by iconic royal paintings, as Rogue Opera presents a fantastic Night at the Opera, taking you on a journey through Bizet, Mozart, Verdi, Puccini and more, weaving a story…
TripAdvisor Traveller Rating
1733 reviews
Taylor Fever Extravaganza

Windsor

Get ready to Shake it Off with Taylor Fever – a spectacular, music packed production celebrating pop sensation Taylor Swift!