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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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Number of results: 19

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TripAdvisor Traveller Rating
1737 reviews
Tours of Theatre Royal Windsor

Windsor

Peek behind the curtain at the historic Theatre Royal Windsor and discover over 240 years of theatrical history on a theatre tour.
TripAdvisor Traveller Rating
1737 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
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.
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TripAdvisor Traveller Rating
253 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
1735 reviews
Cinderella

Windsor

Step into a world of magic and laughter with Cinderella at Theatre Royal Windsor! Starring Kevin Cruise, Steven Blakeley, Michael Praed and more, this dazzling pantomime features songs, slapstick and fairy-tale fun for the whole family. Don’t miss…
The Comet

Maidenhead

When Nyla has to leave her home in the countryside to start life again in the city, all she can think about is everything she misses from before. So when a comet comes crashing through the city streets and starts to glow and grow, Nyla can’t resist…
The Fleetwood Mac Songbook

Maidenhead

The six-piece tribute band perform a spellbinding recreation of the stellar songbook of Fleetwood Mac.
December and January Cinema Screenings at Norden Farm

Maidenhead

Norden Farm Centre for the Arts in Maidenhead have announced their latest cinema line up – and there’s something for everyone this season.
TripAdvisor Traveller Rating
253 reviews
The Royal Ballet: The Nutcracker

Maidenhead

Discover the enchantment of ballet with this sparkling festive treat for the whole family. This is an event cinema screening.
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
1735 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.
Danny O' Brien: Adulting HaЯd!

Windsor

After a sell-out tour last year, multi‑award‑winning Irish comedian comes to The Old Court Theatre with a brand new stand‑up show! Mortgage‑approved, childless millennial O'Brien has just sold out his entire Edinburgh Festival Fringe run and he…
Dancing with the Stars Weekend

Old Windsor

Spend the weekend with your favourite stars of Strictly Come Dancing and British Dance Champions at the impressive De Vere Beaumont Estate.
TITANIC The Musical

Ascot

Step aboard the greatest story ever told on the grandest ship ever built.
Titanic: The Musical isn't about an iceberg - it's about the people who dared to dream. From humble immigrants chasing new beginnings to wealthy socialites relishing a life…
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.
TripAdvisor Traveller Rating
1735 reviews
Allegra

Windsor

Allegra is a moving comedy with spectacular song and dance sequences, but is also a touching and emotional examination of how, sometimes, the most beautiful of minds can start to disappear.
Fi.Fest

Maidenhead

Fi.Fest is a family-friendly summer music festival event that takes place in Fifield, located between Windsor and Maidenhead in Berkshire. Join us on July 10th and 11th for an exciting weekend filled with amazing music and non-stop entertainment.