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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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Reg Meuross - Fire and Dust: Woody Guthrie Story

Maidenhead

Commissioned and produced by Pete Townshend and created by award-winning singer-songwriter - Reg Meuross - Fire and Dust: Woody Guthrie Story is at Norden Farm Centre for the Arts on Friday 10 July at 8pm. Tickets are £23.
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…
Windsor Jazz Club: Debby Bracknell & Stuart Henderson

Alma Road, Windsor

A beautiful musical pairing of international star vocalist Debby Bracknell and melodic trumpet maestro Stuart Henderson. Tonight singing and playing a selection of favourite jazz.
Jazz Jam for players

Alma Road, Windsor

A round circle jam where you get to play all night, and solo on every song. With no audience present, you're free to practise, experiment and develop your style
The Maidenhead Big Weekender

Maidenhead

Get down to Braywick Sports Ground for the 2026 Maidenhead Big Weekender! Join us on Saturday 25th & Sunday 26th July for two unforgettable days of live music, delicious food, exciting entertainment and summer vibes.
Opera in the Garden at Cumberland Lodge

Windsor

Opera's most dangerous love story - re-imagined for an intimate outdoor stage Set against the beautiful backdrop of Cumberland Lodge, Rogue Opera presents a thrilling and intimate re-imagining of Bizet's Carmen.
Windsor Jazz Club: Sarah Bolter Trio

Alma Road, Windsor

Sarah Bolter started with the Johnny Howard Big Band at the Bournemouth Pavilion and, as a teenager, played most weekends with the New Dorset Dance Orchestra. She specialised in jazz alto and classical soprano sax at Southampton University.
Rock the Rec Windsor

Windsor

Rock the Rec Windsor is a music festival organised by Clewer & Dedworth Together CIC, showcasing great music in the heart of Windsor. The event promises a day of incredible live performances, great food, and an electric atmosphere for all ages. Best…
Windsor Jazz Club: Ranglin' - A Musical Salute to Ernest Ranglin

Alma Road, Windsor

Ranglin' is a quartet raising a musical salute to the great Jamaican jazz guitarist Ernest Ranglin. Without a doubt the most accomplished Jamaican musician most people have never heard of. Expect reggae-jazz-calypso-funk grooves rooted down with…
Jazz Sabbath Tour 2026

Windsor

Jazz Sabbath is a jazz trio from Great Britain that plays new jazz arrangements of Black Sabbath songs. Although the band presents itself as a jazz trio founded in 1968 and the original authors of the tracks later made famous by Black Sabbath.
Tom Jones & Friends Tribute night

Maidenhead

Get ready for an unforgettable evening of live entertainment, great food, and vibrant atmosphere at our Tom Jones Tribute Party Night! Your ticket (£40 per person) includes a reserved seat on one of our lively shared round tables (8–10 guests) in…
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Neverland: The Peter Pan Drone Light Show

Windsor

Step into the world of Peter Pan as Peter, Wendy and Tinker Bell take flight in a spectacular drone light show inspired by J.M. Barrie’s classic tale.
George Michael Tribute night

Maidenhead

Join us for an incredible evening of music, dining, and entertainment at our George Michael Tribute Party Night – a celebration of one of pop’s most iconic artists.
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…