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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: 41

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Live Music Lunch Club: Charlotte Spruit (violin)

Maidenhead

Norden Farm Centre for the Arts continues its new regular series of concerts. Its for lovers of live music who prefer their concerts in the daytime, alongside a little lunch, in a relaxed environment. Live Music Lunch Club: Charlotte Spruit (violin)…
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
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…
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
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!
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.
The Simon Spillett Quartet

Maidenhead

A musician who has worn many hats in jazz over his twenty five year career. The Simon Spillett Quartet is at Norden Farm Centre for the Arts on Friday 23 May at 8pm. Tickets are £17.50.
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.…
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.
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
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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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,…
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.
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 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.
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.
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.
Daniele Piroddi - World Music on a Classical Guitar

Vansittart Trading Estate, Windsor

Daniele Piroddi performs an evening of classical guitar music from around the world, including works by Villa-Lobos (Brazil), de Falla (Spain), Theodorakis (Greece), Yukihiro Yoko (Japan) and more.
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.
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…