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La Bouche Manouche featuring Irene Serra

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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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A Christmas Wish

Windsor

The award-winning Let's All Dance Ballet Company is delighted to be back with this gorgeous festive show for young children and families.
Hundred Watt Club – A Festive Evening of Burlesque & Cabaret

Maidenhead

The nights are drawing in, temperatures are dropping so what better way to keep warm on a dark December evening than by spending the night with Hundred Watt Club at their Festive Burlesque Revue?
Baby & Children’s Pre-Loved Sale & Magical Christmas Music Workshop

Vansittart Estate, Windsor

Join us for a festive family morning at Other Space Arts, combining a Baby & Children’s Pre-Loved Sale with a magical interactive Christmas music and storytelling experience.
Christmas at the Quarter

Maidenhead

Bring family and friends along to enjoy a charming Christmas Market, meet Santa in his festive grotto, sip on warming mulled wine, and soak up the atmosphere with live music throughout the day. Stay a little longer and enjoy a festive get-together…
The Nutcracker

Windsor

Back by popular demand, the award-winning Let's All Dance Ballet Company is thrilled to return with their fun festive sparkling production of The Nutcracker, perfect for the whole family.
Stan Tracey's 'A Child's Christmas: Jazz Suite'

Alma Road, Windsor

A Child's Christmas is a festive suite composed in 2011 by Ronnie Scott's resident pianist and Mercury Music Prize nominated recording artist, Stan Tracey.
Christmas Soul Stew

Windsor

Join us for one of our best-loved events. There will be our usual offering of fabulous cocktails, wine and locally brewed beer plus a food truck on site to keep us going!
The Christmas Orchestra

Windsor

The Christmas Orchestra returns for 2026, after a fantastic run of sold-out shows in 2024 and 2025! We're thrilled to be bringing our unique concert experience to more locations than ever before. Prepare to immerse yourself in the magic of the…
Festivo

Windsor

Bringing you the unforgettable sound of Christmas at Windsor Castle, these popular concerts featuring the Choir of St George's Chapel are certain to fill you with festal cheer.
Tinsel

Maidenhead

Tinsel is the tale of one magical little boy who dreams of being the fairy on top of the Christmas tree! He can sing, dance, and wear a sparkly tiara as well as anyone else can. But to get to the top, he’ll have to convince a whole tree of doubting…
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Maidenhead Concert Band Christmas Concert

Maidenhead

Join Maidenhead Concert Band for a sparkling evening of festive music as we welcome the Christmas season. Enjoy a joyful mix of big band, musical theatre and popular classics, along with much‑loved Christmas favourites to get you into the holiday…
André Rieu’s 2026 Christmas Concert: Let It Snow

Maidenhead

This holiday season, celebrate the most wonderful time of the year on the big screen with André Rieu's 2026 Christmas Concert – Let It Snow.
A Night at The Musicals!

Windsor

Join the entire Windsor College Theatre Company as they present 'A Night at The Musicals!' Celebrating the iconic songs and dances from musicals such as Cabaret, The Great Gatsby, Our House, Les Misérables and The Rocky Horror Picture Show.
The Great Big Community Show at Christmas

Maidenhead

A festive celebration showcasing the talent of local groups who call Norden Farm home. Connect with your community and celebrate through song, live music and dance. All tickets go towards the Norden Farm Forever Fund, helping us secure our future…
Carols on the Hill

Windsor

Now in its 77th year, Carols on the Hill is a wonderful evening for the whole family! Carols and Gospel Readings recall the Christmas Story, and a charity collection is introduced by the Royal Borough of Windsor & Maidenhead's Mayor. Music…
Sleeping Beauty

Braywick Road, Maidenhead

This year’s Maidenhead Pantomime, Sleeping Beauty, is jam-packed with magic, music, comedy and plenty of audience participation!
La Bouche Manouche | A Gypsy Jazz Christmas

Maidenhead

La Bouche Manouche featuring Irene Serra invite you to a dazzling evening of festive cheer, blending the timeless elegance of the Great American Songbook with their signature Manouche swing.
Christmas Ceilidh

Maidenhead

Norden Farm Centre for the Arts presents Christmas Ceilidh.
Walking in a Musical Wonderland

Windsor

Back by popular demand, following a sold-out run last year, Walking in a Musical Wonderland returns for another dazzling afternoon of music, laughter and seasonal magic.
Cinderella

Maidenhead

Maidenhead Drama Guild is back with the queen of all Pantomimes, Cinderella. With the help of her best friend Buttons and her Fairy Godmother, will Cinderella make it to the ball, meet the handsome Prince Charming and live happily ever after? Come…