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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

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: 47

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Kate Cheka - A Messiah Comes

Maidenhead

After a sellout at the 2024 Edinburgh Fringe Festival, this award nominated show comes to Maidenhead. Kate Cheka - A Messiah Comes is at Norden Farm Centre for the Arts on Friday 30 May at 8pm. Tickets are £16.50.
Gasper Nali

Maidenhead

This not-so-traditional babatoni player is from the small town of Nkhata Bay on the shore of Lake Malawi. Gasper Nali is at Norden Farm Centre for the Arts on Thursday 29 May at 8pm. Tickets are £17.50.
Jaz Delorean

Maidenhead

He has a colourful past together with a wild and wandering present. Jaz Delorean performs at Norden Farm Centre for the Arts on Friday 6 June at 8pm. Tickets are £19.
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!
Michael Akadiri – Trust Me, I’m a Daddy

Maidenhead

Multi-award-winning comedian and junior doctor brings us his sophomore show. Michael Akadiri – Trust Me, I’m a Daddy is at Norden Farm Centre for the Arts on Saturday 17 May at 8pm. Tickets are £16.50 | £15 NHS
TripAdvisor Traveller Rating
1732 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.
TripAdvisor Traveller Rating
1730 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.
Avalon Edinburgh Preview: Pierre Novellie and Toussaint Douglas

Maidenhead

A double header of comedy as two top comedians warm up ahead of the Edinburgh Festival. Avalon Edinburgh Preview: Pierre Novellie and Toussaint Douglas are at Norden Farm Centre for the Arts on Thursday 5 June at 8pm. Tickets are £13.50.
Sorrel Nation

Maidenhead

Travelling troubadour brings a soulful mix of folk-rock and country. Sorrel Nation performs at Norden Farm Centre for the Arts on Friday 16 May at 7.30pm. Tickets are £16.
TripAdvisor Traveller Rating
1732 reviews
Twist & Shout

Windsor

An all-star cast from the West End deliver a musical powerhouse of a show at Theatre Royal Windsor. It starts with the explosion of Brit Pop in 1962 through to the era of Flower Power and Free Love of the late Sixties.
Fe Fi Fo Farm | Family Theatre in the Park

Ascot

Head into the woods and come and join us down on the farm to enjoy a unique theatre event brought to you by the Handmade Theatre Company. ‘Fe Fi Fo Farm’ is a fun family show packed full of original songs, music and beautiful puppets.
TripAdvisor Traveller Rating
1730 reviews
The Manfreds – Maximum Rhythm ‘N’ Blues

Windsor

The Manfreds, featuring both former lead singers of Manfred Mann, Paul Jones and Mike d’Abo, will be recreating their fabulous Maximum Rhythm ‘N‘ Blues show for one night only at Theatre Royal Windsor!
TripAdvisor Traveller Rating
1730 reviews
Arrival – The Hits of ABBA

Windsor

Calling all Dancing Queens – get ready to embark on a musical journey back to the 70s where disco reigned supreme and ABBA ruled the charts! Arrival – The Hits of ABBA’s multi award-winning show is returning in 2025 following sell out shows in more…
James Church’s Cabaret Night with Cassidy Janson

Maidenhead

An evening with Olivier award-winning actress. James Church’s Cabaret Night with Cassidy Janson is at Norden Farm Centre for the Arts on Saturday 7 June at 8pm. Tickets are £25.50.
The Dumb Waiter by Harold Pinter

Windsor

Two Man Theatre Company—a newly formed duo with a passion for bold, character-driven storytelling. As a company, we're committed to exploring existing works through our own artistic lens, bringing fresh perspective and intent to every production.…
Fi.Fest

Maidenhead

Fi.Fest is a family-friendly festival that promises an unforgettable experience for every member of the family. Choose the camping option, allowing you to enjoy the festivities all weekend long, and make it a festival to remember! Get ready to…
Royal Free Singers Summer Concert with Chiltern Concert Band

Windsor

Windsor Parish Church of St. John the Baptist celebrated its 200th anniversary in 2022. This concert will be part of the launch of the NEXT 200 project which is about planning for the future to make the church a welcoming, accessible, creative,…
Cumberland Lodge Murder Mystery Weekend

Windsor

Step into the roaring twenties for a Murder Mystery weekend like no other. Join us this June for Cumberland Lodge's first-ever Murder Mystery Weekend, set in the glamorous world of 1924.
Big Star - The Nick Skelton Story

Windsor

Preview screening followed by Q&A of Big Star: The Nick Skelton Story.
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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