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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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The Old Court Cinema

Windsor

Discover film screenings at The Old Court Cinema, Windsor. With its big screen, immersive Dolby surround sound and comfortable seating, the Old Court’s cinema in Windsor is your local big screen experience and the perfect place to enjoy a wide…
Jack And The Beanstalk Relaxed Performance

Windsor

Climb into a world of magic, mischief, and massive fun as Theatre Royal Windsor proudly presents Jack And The Beanstalk, the giant of all pantomimes, at a special Relaxed Performance.
Tuesday Music Night at OSA: Live Music Quiz & Blues Jam

Vansittart Estate, Windsor

Two music events, one night at Other Space Arts! Test your knowledge at our interactive Live Music Quiz downstairs or head upstairs for the free Backroom Sessions Blues Jam. Come to play, compete or simply enjoy the music, with pizza plus hot and…
Kenneth Williams: A Centenary Celebration

Maidenhead

2026 is the centenary year of one of Britain’s most distinctive and beloved performers. Kenneth Williams: A Centenary Celebration is at Norden Farm Centre for the Arts on Wednesday 25 November at 7.30pm. Tickets are £19 (plus a £1.90 per transaction…
Epic Soundtracks by Candlelight

Windsor

One duo. One experience. Yoon and Nurry are your international concert soloists for the evening. They are CineDuo – nobody else.
Absolute U2

Windsor

Absolute U2 brings together seasoned musicians, veterans of hundreds of live shows, united by one mission: to recreate the sound, spirit, and electric energy that made U2 legends.
Royal Free Singers with the Orchestra of London

Windsor

Looking forward to Christmas celebrations, our concert programme reflects the messages of Advent: Hope, Peace, Joy and Love. With 5 soloists, we are delighted to be performing beautiful and atmospheric music from three celebrated composers: Paris…
The Snow Queen Puppet Show & Puppet-Making Workshop

Vansittart Estate, Windsor

Step into a magical winter world with Theatrix Arts’ beautiful puppet production of The Snow Queen. Follow Gerda on her adventure to rescue Kai through puppetry, changing scenery, music and sound effects, before meeting the puppets and making your…
A Town Called Christmas

Maidenhead

Buckle in for a rollercoaster of magic, music and mayhem. Clementine crash-lands in a crumbling town where only the long-forgotten fables, a cantankerous caretaker and a glitching robot remain. Can they save the day, and the town called Christmas?
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.
Christmas Karaoke

Windsor

Join the team at the Old Court for an evening of Christmas Karaoke. Dress in your finest festive outfits, Christmas jumpers or hats and choose your favourite Christmas song to share with the crowd!
Festive Soundtracks by Candlelight

Windsor

One duo. One experience. Yoon and Nurry are your international concert soloists for the evening. They are CineDuo – nobody else.
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.
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…
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!
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.