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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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Number of results: 40

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The Vinyl Frontier - Musical Showdowns

Maidenhead

Join host Jeff Lloyd for a new series of monthly vinyl music events at Norden Farm Centre for the Arts this Spring. Tickets are £13.50.
Angela Barnes: Angst

Maidenhead

A brand new stand-up show from Angela Barnes, star of Mock The Week and Live at The Apollo. Angela is a worrier. Whatever it is, she’ll worry about it. But don’t let that worry you – she’ll worry enough for the both of you.
Danny O' Brien: Adulting HaЯd!

Windsor

After a sell-out tour last year, multi‑award‑winning Irish comedian comes to The Old Court Theatre with a brand new stand‑up show! Mortgage‑approved, childless millennial O'Brien has just sold out his entire Edinburgh Festival Fringe run and he…
Lucy Porter - Let Yourself Go!

Maidenhead

Festival favourite Lucy returns with a brand new show about the power of letting yourself go - in every sense.
Michael Jackson Tribute Night

Maidenhead

Celebrate the magic, the moves, and the music of one of the greatest icons of all time — Michael Jackson, the King of Pop. With a legendary career spanning more than four decades, MJ’s influence continues to electrify audiences worldwide.
TripAdvisor Traveller Rating
1736 reviews
Glorious!

Windsor

Dubbed ‘the worst singer in the world’, Glorious! is the true story of American socialite Florence Foster Jenkins, who was known for her flamboyant costumes, enigmatic performances, and decidedly off-key voice.
Royal Free Singers - Fauré: Requiem

Windsor

We invite you to join us for a programme of powerful and exciting music from two significant and highly influential composers: Gabriel Fauré who bridged the eras of late Romanticism and early modernism, and the renowned 20th Century Hungarian…
Rave On - The Ultimate 50s and 60s Experience

Windsor

Rave On – The Ultimate 50s & 60s Experience returns with a brand-new show! Back for another year and jam-packed with more classic hits than ever before. Enjoy note perfect renditions of the most loved sounds from the decades that gifted us Rock and…
Dancing with the Stars Weekend

Old Windsor

Spend the weekend with your favourite stars of Strictly Come Dancing and British Dance Champions at the impressive De Vere Beaumont Estate.
TripAdvisor Traveller Rating
564 reviews
Wildcat Willie’s Music Bingo

Windsor

Forget everything you know about traditional bingo, Wildcat Willie’s Music Bingo is here to turn it all upside down! It’s loud, it’s fun, and best of all… it’s completely free to play.
TITANIC The Musical

Ascot

Step aboard the greatest story ever told on the grandest ship ever built.
Titanic: The Musical isn't about an iceberg - it's about the people who dared to dream. From humble immigrants chasing new beginnings to wealthy socialites relishing a life…
Olaf Falafel’s Stupidest Super Stupid Show

Maidenhead

Winner of the Best Kids’ Show at the 2024 Leicester Comedy Festival. After a sell out run at last year’s Fringe, comedian and children's author Olaf Falafel is dishing up another frying pan full of family-friendly comedy.
The George Harrison Project

Maidenhead

A true musical icon who helped shape the sound of modern music will be celebrated by The George Harrison Project, the ultimate live tribute to the life and music of George Harrison. Catch this special performance at Maidenhead's Norden Farm Centre…
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.
Elton John Tribute Night

Maidenhead

Get ready for a fun-packed, high-energy celebration of Elton John’s greatest hits! Absolutely Elton brings the magic of Sir Elton to the stage with vibrant showmanship and live piano for an authentic, unmistakable sound.
TripAdvisor Traveller Rating
1736 reviews
Allegra

Windsor

Allegra is a moving comedy with spectacular song and dance sequences, but is also a touching and emotional examination of how, sometimes, the most beautiful of minds can start to disappear.
Long Walk Live

Windsor

Brought to you by the team behind Windsor Festival, Long Walk Live (26-27 June 2026) is a brand-new and exciting live music event set against the iconic backdrop of Windsor’s Long Walk, near the iconic Windsor Castle.
Fi.Fest

Maidenhead

Fi.Fest is a family-friendly summer music festival event that takes place in Fifield, located between Windsor and Maidenhead in Berkshire. Join us on July 10th and 11th for an exciting weekend filled with amazing music and non-stop entertainment.
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…
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.