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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

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.

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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TripAdvisor Traveller Rating
1733 reviews
Theatre Royal Windsor

Windsor

The Theatre Royal Windsor is a beautiful Edwardian theatre nestling between Windsor Castle and the River Thames and is the only unsubsidised producing theatre to operate all year round in Britain.
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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Other Space Arts

Windsor

Other Space Arts (OSA) is a grassroots live music and arts venue with a plant-based café, restaurant and bar, open Thursday to Sunday. Located just a short walk from Windsor town centre, OSA hosts original performances, live music and DJs in a…
TripAdvisor Traveller Rating
253 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.
The Windsor Fringe

Windsor

Windsor Fringe is the second oldest fringe in the UK after Edinburgh, and showcases an innovative and affordable programme of music, dance, comedy, drama, art and more!
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
253 reviews
St John’s Chamber Orchestra: Beethoven’s Choral Symphony

Maidenhead

St John’s Chamber Orchestra: Beethoven’s Choral Symphony is at Norden Farm Centre for the Arts on Saturday 11 October at 7.30pm. Tickets are £24 | Under 18s free with an adult.
TripAdvisor Traveller Rating
1733 reviews
Cirque – The Greatest Show, Reimagined

Windsor

Cirque – The Greatest Show has been Reimagined and is back for 2025 – bigger, bolder, and more electrifying than ever! Get ready for a dazzling fusion of musical theatre and jaw-dropping circus acts, taking the original circus-meets-musical-theatre…
Diwali Masti

Maidenhead

Diwali Masti is an evening of music and dance to celebrate the coming of Diwali, the Festival of Lights. The event takes place at Norden Farm Centre for the Arts on Wednesday 15 October at 7.30pm. Tickets are £16 | £14 under 18s | Family and Friends…
Tina Turner on tour at The Ivy

Windsor

An Icon Reimagined. A Legacy Celebrated. Step into an unforgettable evening of glamour, soul, and sheer musical brilliance with TINA at The Ivy, from 7pm to 9pm.
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…
The Haar

Maidenhead

The Haar bring their radically fresh, boundary-pushing take on traditional songs to Norden Farm Centre for the Arts on Friday 17 October at 8pm. Tickets are £22.
Never 42

Maidenhead

The UK’s number one Level 42 tribute return to Maidenhead to bring Level 42’s music live. Never 42 are at Norden Farm Centre for the Arts on Saturday 18 October at 8pm. Tickets are £20.50
TripAdvisor Traveller Rating
1733 reviews
The Shires – The 2 Of Us Tour

Windsor

The UK’s biggest country music export The Shires have announced an intimate acoustic tour for 2025. The two of us tour will see Ben Earle and Crissie Rhodes tour the length and breadth of the UK performing all their classic tracks. Book to see them…
Maidenhead Town Show

Maidenhead

Discover Maidenhead Town Show: it's baking, cooking, barking, crafting, singing, dancing and general family fun!
TripAdvisor Traveller Rating
1733 reviews
Buddy – The Buddy Holly Story

Windsor

This sensational multi award-winning West End show first opened in 1989 and has been thrilling audiences around the world ever since. Now it triumphantly returns to Theatre Royal Windsor as part of its 2025/26 UK Tour.
Carmen the Musical

Maidenhead

Carmen is one of the most popular operas of all time, and this accessible yet audacious reimagining of Bizet's masterpiece is a treat for both lovers of opera and musical theatre alike.
Come From Away

Windsor

WMTC Productions presents Come From Away - Welcome to the Rock.
Moscow Drug Club

Maidenhead

Moscow Drug Club bring a heady mix of jazz, French musette, Latin grooves and New Orleans swing to Norden Farm Centre for the Arts on Thursday 23 October at 8pm. Tickets are £20.
Autumn Cinema screenings from National Theatre Live at Norden Farm

Maidenhead

National Theatre Live bring some of the most talked about plays to the big screen and you can see them at Norden Farm Centre for the Arts in Maidenhead this Autumn. Tickets are £17.