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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
1748 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
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.
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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Windsor Jazz Club: Ranglin' - A Musical Salute to Ernest Ranglin

Alma Road, Windsor

Ranglin' is a quartet raising a musical salute to the great Jamaican jazz guitarist Ernest Ranglin. Without a doubt the most accomplished Jamaican musician most people have never heard of. Expect reggae-jazz-calypso-funk grooves rooted down with…
Late Summer Cinema at Norden Farm

Maidenhead

The summer season is in full swing at Norden Farm Centre for the Arts – and the Maidenhead based entertainment venue are excited to announce their latest cinema line up.
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.
National Theatre Live: The Misanthrope

Maidenhead

Award-winning Sandra Oh (Killing Eve) plays the title role in this razor-sharp reimagining of Molière’s classic dark comedy. Filmed live on stage at the National Theatre, Indhu Rubasingham directs Martin Crimp’s (Cyrano de Bergerac) highly…
The Windsor Fringe

Windsor

The Windsor Fringe is the second oldest fringe in the UK after Edinburgh. Run by volunteers, it offers an innovative and affordable programme of music, dance, comedy, drama and art with a passion for being a platform for promoting new talent.
Tom Jones & Friends Tribute night

Maidenhead

Get ready for an unforgettable evening of live entertainment, great food, and vibrant atmosphere at our Tom Jones Tribute Party Night! Your ticket (£40 per person) includes a reserved seat on one of our lively shared round tables (8–10 guests) in…
Rebeca Ortega Flamenco: Beyond Borders

Maidenhead

After capturing the hearts of Maidenhead audiences with the pure passion of Raíces and earning award nominations for her deeply reflective, multidisciplinary production La Rebelidía del Silencio (The Rebellion of Silence), Rebeca Ortega returns to…
Dez Eze Jazz Rock Night

Windsor

Veteran guitarist Ronnie Johnson, known for decades of work with Van Morrison, Joe Cocker and others, joins forces with his guitarist son Patrick Johnson, bassist Dylan Bond, and drummer Neil Burton in a new instrumental project exploring…
TripAdvisor Traveller Rating
1748 reviews
The Anastasia File

Windsor

Jenny Seagrove (Judge John Deed) reprises her critically acclaimed performance in Royce Ryton’s The Anastasia File, as part of The Theatre Royal Windsor Season on tour.
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…
MoonAge - The Best of Bowie Tribute Band

Windsor

Welcome to MoonAge, the premier David Bowie tribute band in the UK. With a repertoire that spans Bowie's iconic hits, we capture the essence and spirit of one of music's greatest legends.
TripAdvisor Traveller Rating
531 reviews
Neverland: The Peter Pan Drone Light Show

Windsor

Step into the world of Peter Pan as Peter, Wendy and Tinker Bell take flight in a spectacular drone light show inspired by J.M. Barrie’s classic tale.
Rachael McShane and The Cartographers

Maidenhead

Prepare for a powerful blend of traditional folk and contemporary sounds as Rachael McShane and The Cartographers come to Norden Farm Centre for the Arts on Saturday 3 October at 8pm. Tickets are £18.50 (plus a £1.90 per transaction booking fee).
TripAdvisor Traveller Rating
1748 reviews
Wilko: Love And Death ‘N’ Rock And Roll

Windsor

In 2012, Wilko Johnson, the iconic rock star and founder of legendary Essex band Dr Feelgood, was told he had inoperable cancer and a year to live. Refusing all treatment, he decided to spend his last months living meaningfully: seeing the people,…
An Evening of Comic Strip with Peter Richardson & Guest(s)

Maidenhead

An Evening of Comic Strip with Peter Richardson & Guest(s) is at Norden Farm Centre for the Arts on Tuesday 6 October at 8pm. Tickets are £21.50 (plus a £1.90 transaction booking fee).
Finlay Christie: Champagne Casanova

Maidenhead

Comedian well known on YouTube and TikTok comes to Maidenhead. Finlay Christie: Champagne Casanova is at Norden Farm Centre for the Arts on Friday 9 October at 8pm. Tickets are £19.50 (plus a £1.90 per transaction booking fee).