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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.

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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TripAdvisor Traveller Rating
1733 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
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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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…
Live at the Bandstand

Windsor

Come and enjoy live band performances in the open air this summer. Windsor and Eton Business Partnership presents Windsor’s Live at the Bandstand programme 2025.
TripAdvisor Traveller Rating
252 reviews
Shaparak Khorsandi: Scatterbrain

Maidenhead

Shappi Khorsandi is a comedian, author, speaker and advocate for human rights. She established herself as one of the UK’s finest comedians with her sell-out Edinburgh show, Asylum Speaker. Shappi’s sensitive yet witty exploration of her experiences…
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…
Carl Donnelly - Another Round

Maidenhead

Turning life’s darkest moments into comedy gold. Carl Donnelly - Another Round is at Norden Farm Centre for the Arts on Friday 12 September at 8pm. Tickets are £17.50. Age guidance 15+ years.
TripAdvisor Traveller Rating
1733 reviews
Walk Like A Man

Windsor

Walk Like A Man is the ultimate celebration of Frankie Valli & The Four Seasons, recreating the iconic powerful falsetto with perfection.
The Rymatones

Maidenhead

Local classic Rock n Roll band with special guest. The Rymatones perform at Norden Farm Centre for the Arts on Tuesday 16 September at 8pm. This is a standing event with some unallocated seating. Tickets are £16.50.
Norden Farm Forever Gala

Maidenhead

Join us for an incredible evening’s entertainment at our Norden Farm Forever Gala on Wednesday 17 September. This is a show stopping anniversary event. It celebrates 25 years of the much-loved multi-arts venue and launches the Norden Farm Forever…
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
1733 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.
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…