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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
255 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
1750 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.
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…
The Old Court Artspace & Firestation Bar

Windsor

The Old Court Artspace & Firestation Bar is Windsor's community cultural hub, housed in a magnificent Edwardian building that has been at the heart of civic life since 1907. Originally home to Windsor's police station, magistrates' court and fire…
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Diwali Masti

Maidenhead

Diwali Masti is an evening of music and dance to celebrate the coming of Diwali, the Indian Festival of Lights. The event takes place at Norden Farm Centre for the Arts on Wednesday 4 November at 7.30pm. Tickets are £16 | £14 under 18s | Family and…
I Love You, You're Perfect, Now Change

Windsor

A hilarious and heartwarming exploration of love, dating, and relationships, I Love You, You're Perfect, Now Change takes audiences through the ups and downs of romance - from first dates to marriage and beyond.
Frank Sinatra Big Band Bash!

Maidenhead

Award-winning singer Robert Habermann presents a programme of some of Frank Sinatra’s greatest hits.
James Church’s Cabaret Night with Fra Fee

Maidenhead

West End musical director hosts a sparkling evening of musical theatre. James Church’s Cabaret Night with Fra Fee is at Norden Farm Centre for the Arts on Saturday 7 November at 8pm. The evening features acclaimed stage and screen star Fra Fee and…
Kirsty McGee & Nina Freckles – Live Folk Music at Other Space Arts, Windsor

Windsor

Join Other Space Arts for a special family-friendly afternoon of live folk music, original songwriting and musical storytelling in Windsor. Acclaimed British singer-songwriter Kirsty McGee joins German-Brazilian artist Nina Freckles for an intimate…
The Royal Ballet and Opera in Covent Garden | Screenings at Norden Farm

Maidenhead

The Royal Ballet and Opera in Covent Garden is the at the heart of London and British cultural life. Exciting productions are brought to the cinema screen at Norden Farm Centre for the Arts this season. Tickets are £17 (plus a £1.90 per transaction…
TripAdvisor Traveller Rating
1748 reviews
A Man For All Seasons

Windsor

Direct from the West End, the greatest, most powerful and dangerous figures who shaped English history are brought vividly to life in Robert Bolt’s award-winning play.
Caitlin O’Ryan - At What Point Poetry Tour

Maidenhead

At what point do we figure it out // does it get easier // will we find the answers // will I feel okay? Caitlin O’Ryan - At What Point Poetry Tour is at Norden Farm Centre for the Arts on Wednesday 11 November at 8pm. Tickets are £15.50 (plus a £1…
Alasdair Beckett-King: King of Crumbs

Maidenhead

Come vagabonds, come mountebanks, come coney-catchers and cutpurses and meet the King of Crumbs! Alasdair Beckett-King: King of Crumbs is at Norden Farm Centre for the Arts on Thursday 12 November at 8pm. Tickets are £21.50 (plus a £1.90 per…
High Spirits! Ghost Walk in Windsor

Windsor

With Debbie Keenan as your guide this Halloween, walk the streets of a town that has seen hangings and burnings at the stake, as you hear stories of strange sightings in Windsor Great Park and a royal ghost spotted by Queen Elizabeth II.
John Horler Trio – Celebrating Bill Evans

Maidenhead

John Horler is a British jazz legend. He has played with everyone from Chet Baker to Dame Cleo Lane; Sir John Dankworth to Maynard Ferguson – the who’s who of British jazz stars. This special show celebrates the music, legacy and genius of pianist…
Rosie Holt: The Illegal Aliens Have Landed!

Maidenhead

Rosie and her MP alter-ego are back, fighting their biggest foe yet. Rosie Holt: The Illegal Aliens Have Landed! is at Norden Farm Centre for the Arts on Saturday 14 November at 8pm. Tickets are £21.50 (plus a £1.90 per transaction booking fee).
Windsor Jazz Club: Eriko Ishihara Trio

Alma Road, Windsor

A fine singer and an excellent jazz pianist Eriko has established an enviable reputation on the UK jazz scene, working at the likes of Ronnie Scott's, 606 Club and the Royal Festival Hall, as well as major concert halls in Hong Kong and Korea.
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
Mary Shelley's Frankenstein

Windsor

Windsor Theatre Guild (WTG) presents Mary Shelley's Frankenstein, a thought-provoking thriller that will haunt your dreams for days to come.
BIRD

Maidenhead

BIRD is the stage sequel to critically acclaimed dance film Catch The Bird Who Won’t Fly, choreographed by Amina Khayyam. This critically acclaimed show is a winner of the Lustrum Award at the Edinburgh Festival Fringe 2023.