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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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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.
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!
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…
Brazen Hodgepodge

Windsor

Brazen Hodgepodge is a sketch comedy show! A fast-paced evening of original sketch comedy scenes and songs. Whether it's current events or loathesome public figures, absurd situations or very familiar social problems, we will make fun of all of it.…
The Wedding Singer

Windsor

SWMTC Productions, the company who brought you the award-winning production of Shout! The Mod Musical and Sister Act present: The Wedding Singer.
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.
Puss in Boots

Windsor

Based on the original version by Charles Perrault, the Let's All Dance Ballet Company brings a new version of Puss in Boots about a friendship between a magical cat and a young man with a talent for music.
TripAdvisor Traveller Rating
252 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.
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
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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Little Shop of Horrors

Windsor

Come and join Windsor College Theatre Company down on Skid Row for the smash hit musical Little Shop of Horrors.
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.
Legally Blonde - The Musical

Windsor

Windsor College Theatre Company present the smash hit musical Legally Blonde. Music and Lyrics by Laurence O'Keefe and Nell Benjamin, Book by Heather Hach Based on the novel by Amanda Brown and the Metro-Goldwyn-Mayer motion picture