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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: 56

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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
1733 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
1733 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
1733 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
1733 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
1733 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…
TripAdvisor Traveller Rating
1733 reviews
Mercury – The Ultimate Queen Tribute

Windsor

Strap yourself in for the ultimate tribute to Freddie Mercury and Queen at Theatre Royal Windsor! With more than 25 years on the road, Mercury guarantee an unforgettable night of music and tells the story of one of the greatest bands in history.
TripAdvisor Traveller Rating
1735 reviews
Whitney – The Candlelight Concert

Windsor

Prepare for an electrifying night at Theatre Royal Windsor as Xperience Live presents Whitney – The Candlelight Concert, bringing you the unforgettable music of Whitney Houston in a tribute like no other!
TripAdvisor Traveller Rating
1733 reviews
Cinderella

Windsor

Get ready to be whisked away to a world of magic, mischief and make-believe! Theatre Royal Windsor proudly presents the spectacular pantomime, Cinderella, for the winter 25/26 season.
Royal Free Singers - Concorde: An Anglo-French Choral Celebration

Windsor

We invite you to join us for an evening of music to honour the masters of the English and French choral repertoires.
The Comet

Slough

Curve Venue announces its Christmas show this year – a production rooted in Slough’s creativity. The Comet is based on the book of the same name by Joe Todd Stanton. It runs from Tuesday 16 December – Wednesday 24 December. Tickets are £14 | £12…
TripAdvisor Traveller Rating
1735 reviews
Jack off the Beanstalk

Windsor

This January, get ready for the udderly cheeky, naughtiest version of Jack and the Beanstalk you’ve ever dared to see!
TripAdvisor Traveller Rating
1735 reviews
Barnum – The Circus Musical

Windsor

Step right up and enter the dazzling world of PT Barnum, where imagination and ambition know no bounds. Hand in hand with wife Charity, Barnum’s life and career twists and turns as he schemes and dreams his way to headier heights.
TripAdvisor Traveller Rating
1733 reviews
Queenz – Drag Me To The Disco!

Windsor

Not just another drag show, Queenz is a trailblazing live vocal drag sensation that has taken the world by storm.
Donaheys Dancing With The Stars Weekend Experience Windsor

Windsor

Spend the weekend with our Dancing Stars at the stunning 4* De Vere Beaumont Estate in Berkshire. Join Strictly Come Dancing Judge Anton du Beke, Strictly Pro Michelle Tsiakkas and Simone Arena, Kai Widdrington, Lauren Oakley, Giovanni Pernice…
Cookham Festival

Cookham, Maidenhead

The Cookham Festival is a celebration of the arts by the village, for the village with over 40 events taking place over the festival fortnight.