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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
1744 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
1744 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…
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.
Summer Cinema at Norden Farm

Maidenhead

Summer has arrived and Norden Farm Centre for the Arts in Maidenhead are excited to announce their latest cinema line up - featuring some of the most talked about films of the moment.
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.
American Concerts

Windsor

We’re delighted to welcome a series of talented American high school bands and choirs to Windsor this June, as part of their international tour! Enjoy FREE open-air performances in some of Windsor’s most iconic settings – the perfect way to add a…
M G Boulter and Samantha Whates

Maidenhead

Respected and critically acclaimed singer songwriters M G Boulter and Samantha Whates are at Norden Farm Centre for the Arts on Friday 26 June at 8pm. Tickets are £16.50.
The Sounds of Bossa Nova with Mario Bakuna

Vansittart Estate, Windsor

Join us for an enchanting evening of Brazilian jazz and Bossa Nova with internationally acclaimed guitarist, vocalist and composer Mario Bakuna.
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.
Choir Concert - BeVox on tour! - Live at the Bandstand

Windsor

Join BeVox on tour from Sheffield and Lincoln for a special outdoor performance at the Bandstand at Alexandra Gardens in Windsor as part of the 'Live at the Bandstand' summer concert series.
Asia Cup Polo International Weekend

Bracknell

Join us on the Final day of the 20th anniversary of the Asia Cup Polo International Weekend
Choir Concert - BeVox on tour! - Windsor Dog Show

Windsor

Join Bevox on tour from Sheffield and Lincoln for a special outdoor performance at the 2026 Windsor Dog Show https://windsordogshow.com/ (included in entry fee).
An Evening with Queen at Royal Windsor Racecourse

Windsor

If you Want to Break Free of the usual routine, why not rock out on the lawn after an evening of great horseracing action here at Windsor Racecourse.
Simon Evans is Staring at the Sun

Maidenhead

Simon Evans is Back! Waaaay back…Simon Evans is Staring at the Sun returns to Norden Farm Centre for the Arts on Thursday 2 July at 8pm, after a sell-out show earlier this year. Tickets are £19.50.
The Phonics

Maidenhead

With more than four times the number of shows than any other Stereophonics tribute - The Phonics are at Norden Farm Centre for the Arts on Friday 3 July at 8pm. Tickets are £20.