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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...Read More

Enjoy some arts and culture in Windsor and Maidenhead

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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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…
TripAdvisor Traveller Rating
1732 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!
Windsor Morris

Windsor

Windsor Morris is a female team of dancers. Come and watch our performances in Windsor town centre. Or come and try morris dancing at one of our taster sessions.
Dire Streets

Maidenhead

They bring to life the classic songs of one of the world’s greatest guitar bands. Dire Streets are at Norden Farm Centre for the Arts on Friday 18 July at 8pm. Tickets are £21.50.
Freddie Gavita

Maidenhead

Winner of the British Jazz Awards Best Trumpeter of 2017. Freddie Gavita performs at Norden Farm Centre for the Arts on Friday 18 July at 8pm. Tickets are £17.50.
The Britpop Hour with Marc Burrows

Maidenhead

Join award-winning comedian for a celebration of music’s most iconic and enduring moments. The Britpop Hour with Marc Burrows is at Norden Farm Centre for the Arts on Saturday 19 July at 8pm. Tickets are £15.50.
The George Washingmachine Quartet

Maidenhead

Known for his virtuosic high-energy violin playing and engaging stage presence. The George Washingmachine Quartet is at Norden Farm Centre for the Arts on Saturday 19 July at 8pm. Tickets are £17.50.
The Maidenhead Big Weekender

Maidenhead

Get ready for two unforgettable days of live music, delicious food, exciting entertainment and summer vibes as part of The Maidenhead Big Weekender.
Must See Movies: Some Like It Hot

Maidenhead

Join your host Jeff Lloyd as he revisits Marilyn Monroe’s signature film. Must See Movies: Some Like It Hot is at Norden Farm Centre for the Arts on Friday 25 July at 8pm. Tickets are £13.50.
Professor Slug’s House of Bugs

Maidenhead

Join the Professor for a colourful show all about bugs. Professor Slug’s House of Bugs is at Norden Farm Centre for the Arts on Tuesday 29 July and Wednesday 30 July at 11.30am. Tickets are £13.50 | Under 16s £11.50 | Family and Friends £45.
TripAdvisor Traveller Rating
1734 reviews
The Enormous Crocodile

Windsor

This august The Enormous Crocodile is weaving his way through the jungle to Theatre Royal Windsor in search of delicious little fingers and squidgy podgy knees…Only the other jungle creatures can foil his secret plans and clever tricks, but they’re…
Hansel & Gretel the Ballet

Windsor

The Let's All Dance ballet company presents this captivating new ballet, adapted from the original Brothers Grimm fairytale.
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…
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
1734 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
1734 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.
Windsor and Eton Living Advent Calendar

Windsor and Eton

Enjoy a different 15-minute live performance every evening of Advent with the Windsor and Eton Living Advent Calendar. Performances will range from songs, carols, music, poetry, book excerpts, creative arts, notes from local history or folklore,…
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.