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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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TripAdvisor Traveller Rating
1740 reviews
Tours of Theatre Royal Windsor

Windsor

Peek behind the curtain at the historic Theatre Royal Windsor and discover over 240 years of theatrical history on a theatre tour.
TripAdvisor Traveller Rating
1740 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
254 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.
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…
Morris Dancing in Windsor on Tuesday 22nd July!

Windsor

North-West style (clog) morris dancing from local team Taeppa's Tump, who are based in Maidenhead. Come and enjoy colourful traditional English dance and music!
Graffiti Classics – The Comedy String Quartet

Maidenhead

16 strings, eight dancing feet and four voices in one electrifying and hilarious musical show! Graffiti Classics – The Comedy String Quartet is at Norden Farm Centre for the Arts on Wednesday 3 June at 7.30pm. Tickets are £23.50.
Jazz Vanguard

Windsor

Jazz Vanguard are a fantastic group of top-notch jazz musicians who are making waves on the jazz scene. They're not just limited to jazz; they've performed in all sorts of genres, and their members have graced some of the biggest venues like Ronnie…
Summer Piano Series (1 of 4): Henry Cash

Maidenhead

The first of a series of classical piano concerts - Summer Piano Series (1 of 4): Henry Cash is at Norden Farm Centre for the Arts on Wednesday 10 June at 7.30pm. Tickets are £19 | Under 18’s free with an adult.
The Specials Ltd

Maidenhead

The most authentic tribute to 2-Tone Ska legends - The Specials Ltd are at Norden Farm Centre for the Arts on Friday 12 June at 8pm. Tickets are £22. This is a standing / dancing event with some unallocated seating.
Haven’t Stopped Dancing Yet!

Maidenhead

Haven’t Stopped Dancing Yet! bring their the fabulous, feelgood 70s and 80s disco night for grown ups back to Norden Farm Centre for the Arts on Saturday 13 June at 8pm. Tickets are £21.50.
TripAdvisor Traveller Rating
1740 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.
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 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…
Live at the Bandstand

Windsor

Come and enjoy live band performances in the open air this summer. Windsor and Eton Business Partnership presents Windsor’s Live at the Bandstand programme 2026.
Windsor & Maidenhead Symphony Orchestral Concert

Binfield

Family Orchestral Concert
Cinema screenings from National Theatre Live at Norden Farm

Maidenhead

Discover some of the biggest plays brought to the big screen from National Theatre Live at Norden Farm Centre for the Arts this summer. Tickets are £17.
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.
Royal Free Singers - Summer Concert with South Coast Singers from California

Windsor

We're delighted to be joined by this talented visiting choir to bring you a light programme of uplifting music, perfect for a summer evening.
The Vinyl Frontier

Maidenhead

Host Jeff Lloyd is back with a brand-new season of monthly vinyl music events this summer at Norden Farm Centre for the Arts. Tickets are £13.50.