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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
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
1746 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.
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.
Children's Summer Theatre Week in Datchet – Ages 8+

Datchet

Five fun-filled days of acting, characters, comedy and movie-inspired scenes, culminating in a live showcase for families on Friday afternoon. Open to all children aged 8+, with no previous experience required.
TripAdvisor Traveller Rating
254 reviews
Summer Camps at Norden Farm

Maidenhead

Norden Farm Centre for the Arts is the place to keep children entertained this summer. They have the perfect opportunity for youngsters try something new in either a Circus Camp, Art Camp or Theatre Camp.
Rapunzel

Maidenhead

A bold and funny adaptation of the much-loved storybook - Rapunzel is at Norden Farm Centre for the Arts on Wednesday 5 and Thursday 6 August at 11.30am and 2pm. Tickets are £13.50 | £11.50 Under 16s | £45 Family and Friends (4 people).
Summer Piano Series (3 of 4): Tomos Boyles

Maidenhead

The Welsh pianist embraces one of Schumann’s most poetic scores and a dramatic war-time sonata by Prokofiev. Summer Piano Series (3 of 4): Tomos Boyles is at Norden Farm Centre for the Arts on Wednesday 5 August at 7.30pm. Tickets are £19 | Under…
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.
Flash - A Tribute to Queen

Maidenhead

Hit after hit, anthem after anthem, guaranteed to blow your mind. Flash - A Tribute to Queen are at Norden Farm Centre for the Arts on Thursday 6 August at 8pm. Tickets are £23.50.
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.
Steve Waterman’s Latin Quartet

Maidenhead

Norden Farm Jazz Club presents Steve Waterman’s Latin Quartet at Norden Farm Centre for the Arts on Friday 7 August at 8pm. Tickets are £17.50.
The JJ Cale Story

Maidenhead

Immerse yourself in the captivating world of rhythm and blues. The JJ Cale Story is at Norden Farm Centre for the Arts on Saturday 8 August at 8pm. Tickets are £17.50.
Brooks Williams and Aaron Catlow

Maidenhead

Enjoy the fiery, fearless sound of Americana, folk and country blues as Brooks Williams and Aaron Catlow come to Norden Farm Centre for the Arts on Thursday 13 August at 8pm. Tickets are £16.50.
Uptown Joel

Maidenhead

Supported by a five-piece live band, the outstanding Darren Reeves brings his all-new hit musical production Uptown Joel to Norden Farm Centre for the Arts on Saturday 15 August at 8pm. Tickets are £26.50.
Opera in the Garden at Cumberland Lodge

Windsor

Opera's most dangerous love story - re-imagined for an intimate outdoor stage Set against the beautiful backdrop of Cumberland Lodge, Rogue Opera presents a thrilling and intimate re-imagining of Bizet's Carmen.
Windsor Jazz Club: Sarah Bolter Trio

Alma Road, Windsor

Sarah Bolter started with the Johnny Howard Big Band at the Bournemouth Pavilion and, as a teenager, played most weekends with the New Dorset Dance Orchestra. She specialised in jazz alto and classical soprano sax at Southampton University.
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