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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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Number of results: 48

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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…
TripAdvisor Traveller Rating
1732 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
1732 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
1732 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!
TripAdvisor Traveller Rating
1732 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…
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
1732 reviews
Taylor Fever Extravaganza

Windsor

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

Windsor

Surinderella is a spectacular all-singing, all-dancing tale set in the Bolly-Woods, where the naach is non-stop, the drama is bigger than your aunties’, and the romance is straight out of a filmi blockbuster!
TripAdvisor Traveller Rating
1732 reviews
Cirque – The Greatest Show, Reimagined

Windsor

Cirque – The Greatest Show has been Reimagined and is back for 2025 – bigger, bolder, and more electrifying than ever! Get ready for a dazzling fusion of musical theatre and jaw-dropping circus acts, taking the original circus-meets-musical-theatre…
TripAdvisor Traveller Rating
1732 reviews
The Shires – The 2 Of Us Tour

Windsor

The UK’s biggest country music export The Shires have announced an intimate acoustic tour for 2025. The two of us tour will see Ben Earle and Crissie Rhodes tour the length and breadth of the UK performing all their classic tracks. Book to see them…
TripAdvisor Traveller Rating
1732 reviews
Buddy – The Buddy Holly Story

Windsor

This sensational multi award-winning West End show first opened in 1989 and has been thrilling audiences around the world ever since. Now it triumphantly returns to Theatre Royal Windsor as part of its 2025/26 UK Tour.
TripAdvisor Traveller Rating
1734 reviews
Some Guys Have All The Luck

Windsor

Celebrating the 80th birthday of Sir Rod Stewart, Some Guys Have All The Luck – The Rod Stewart Story brings to the Theatre Royal Windsor stage an incredible live concert celebrating one of the UK’s most influential icons.
Sherlock Holmes: The Hunt for Moriarty

Windsor

A thrilling adventure based on the work of Sir Arthur Conan Doyle, Sherlock Holmes: The Hunt for Moriarty is a world premiere combining powerful performances, a haunting soundscape and innovative design for an exhilarating theatrical experience.
High Spirits! Ghost Walk in Windsor

Windsor

With Debbie Keenan as your guide this Halloween, walk the streets of a town that has seen hangings and burnings at the stake, as you hear stories of strange sightings in Windsor Great Park and a royal ghost spotted by Queen Elizabeth II.
TripAdvisor Traveller Rating
1732 reviews
A Fairytale For Christmas

Windsor

‘Tis the season to be jolly as the ultimate Irish Christmas concert is back at Theatre Royal Windsor for 2025!
TripAdvisor Traveller Rating
1732 reviews
A Christmas Carol Ballet

Windsor

This Christmas at Theatre Royal Windsor, Ballet Theatre UK is thrilled to present the return of the beloved classic A Christmas Carol, back by popular demand!
TripAdvisor Traveller Rating
1734 reviews
Don’t Dilly Dally!

Windsor

Book your tickets for an afternoon of songs and laughter, as we bring the UK’s best Music Hall acts to Windsor for a unique and entertaining show, accompanied by special guests to be announced.
TripAdvisor Traveller Rating
1732 reviews
Griff Rhys Jones – The Cat’s Pyjamas

Windsor

Griff Rhys Jones is back on the road with the second tour of his much-anticipated brand-new stand-up show, following a hugely successful run last year. Join Griff at Theatre Royal Windsor as he shares more funny observations and comic stories.
TripAdvisor Traveller Rating
1732 reviews
John Barrowman – Camp as Christmas

Windsor

This Christmas join John Barrowman for a brand-new show bursting with festive favourites, showstopping tunes and plenty of glitz. Known for his dazzling voice and infectious energy, John brings you an evening of laughter, music and heartwarming…