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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: 29

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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
1738 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
1738 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
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.
Norden Farm Jazz Club: Nic Meier’s World Group

Maidenhead

Nic Meier is a UK based musician who has carved out a reputation as one of the world’s most original and uniquely talented guitarists. See Nic perform live at Norden Farm Jazz Club: Nic Meier’s World Group at Norden Farm Centre for the Arts on…
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.
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 Upbeat Beatles

Maidenhead

Step back in time and experience the magic of one of the UK’s leading and longest running Beatles tribute shows. The Upbeat Beatles are at Norden Farm Centre for the Arts on Friday 1 May at 8pm. Tickets are £25.50.
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.
Symphonic ABBA

Windsor

The Thames Valley Festival Orchestra returns to Windsor Parish Church, High St, Windsor, Berkshire on May 2, 2026 to perform Louis Clark's 'Symphonic ABBA' arrangements. This follows performances of their highly popular programmes of 'An Evening of…
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…
Tom Houghton - Deep

Maidenhead

Stand-up comedian Tom Houghton returns to Maidenhead with his latest show Deep. Join him at Norden Farm Centre for the Arts on Thursday 7 May at 8pm. Tickets are £21.50.
Nightcaps

Windsor

Don't miss your chance to see the incredible Nightcaps, usually only available for private hire, live at The Old Court. Get ready for a night that's guaranteed to deliver packed dancefloors, unforgettable memories, and a stylish mix of soul and pop…
Windsor Morris

Windsor

Windsor Morris is a female team of dancers. Come and watch our performances in Windsor town centre. Or come and try morris dancing at one of our taster sessions.
Windsor Jazz Club: Michael Wilkins Quartet

Alma Road, Windsor

Michael Wilkins Trained at Birmingham Conservatoire and Leeds College Of Music. He is a regular soloist at The Rose And Crown in Oxford, Goring Community Jazz Club, Ma Bessie's Pig Foot Band, as well as guest soloist at Windsor's Jazz Vanguard. He…
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
Full Range Embassy Day/Night Party

Vansittart Estate, Windsor

Resident at Brixton's legendary Dogstar, Medicine Bar and The Blag Club, Full Range Embassy is back after an awesome event last August, for a second day (and night) party at Other Space Arts.
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.
The Butterfly House

Ascot

This May experience a unique family theatre in the park. Follow the path into the woods at Tom Green's field, bring a picnic and a rug, and get cosy under the trees. "The Butterfly House" is a show that is inspired by nature and packed full of…