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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
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
36 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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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
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…
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.
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
TripAdvisor Traveller Rating
1744 reviews
We Will Rock You

Windsor

Following the success of our previous community production Grease the Musical we’re thrilled to announce our most electrifying summer project yet: We Will Rock You – The Musical, featuring the iconic music of Queen and a bold, futuristic storyline…
Live and Local: Summer Sounds

Maidenhead

This August, Waterside Quarter is excited to host the return of Live and Local: Summer Sounds, in partnership with Maidenhead Festival. Following the success of last year's debut event, the festival is back with an expanded programme, larger…
Jazz Dynamos

Maidenhead

Jazz Dynamos bring their artistic re-imaginings of well-known songs to Norden Farm Centre for the Arts on Thursday 27 August at 8pm. Tickets are £20.
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.
Rock the Rec Windsor

Windsor

Rock the Rec Windsor is a music festival organised by Clewer & Dedworth Together CIC, showcasing great music in the heart of Windsor. The event promises a day of incredible live performances, great food, and an electric atmosphere for all ages. Best…
Lightnin’ Willie and the Poorboys

Maidenhead

Celebrating the true sounds of American blues, Lightnin’ Willie and the Poorboys are at Norden Farm Centre for the Arts on Wednesday 2 September at 8pm. Tickets are £17.50.
Royal Free Singers - Open Evening

Windsor

Come and sing with us at the first rehearsal of our new term. This is an informal evening of singing and an introduction to music for our next concert. Find out if our friendly community choir is for you!
Norden Farm Jazz Club: Alan Barnes Quartet with the Alex Hutton Trio

Maidenhead

Alan Barnes is a prolific international performer, composer, arranger, bandleader and touring soloist. Join him for the Norden Farm Jazz Club: Alan Barnes Quartet with the Alex Hutton Trio at Norden Farm Centre for the Arts on Friday 4 September at…
The Sounds of the 60s with The Zoots

Maidenhead

The golden era of rock and roll returns - The Sounds of the 60s with The Zoots is at Norden Farm Centre for the Arts on Saturday 5 September at 8pm. Tickets are £23.50.
Summer Piano Series (4 of 4): Gabrielé Sutkuté

Maidenhead

Lithuanian-born pianist Gabrielé Sutkuté comes to Maidenhead for the Summer Piano Series (4 of 4): Gabrielé Sutkuté at Norden Farm Centre for the Arts on Wednesday 9 September at 7.30pm. Tickets are £19 | Under 18’s free.
Jane Eyre

Windsor

Conn Artists Theatre Company in association with Theatre Royal Winchester: Part of Play To The Crowd present Charlotte Bronte’s Jane Eyre, Adapted by Nick Young & Ross Muir
Theatre Royal Windsor | Tuesday 15 – Saturday 19 September 2026
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…
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.