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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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Windsor Jazz Club: Nigel Price Trio

Alma Road, Windsor

Nigel Price has performed at Ronnie Scott's more than 500 times and won best guitarist in the 2016 British Jazz Awards. His Organ Trio - nominated for a Parliamentary Jazz Award in 2021 - has recently completed a 46 date nationwide tour of their new…
Step into the World of Opera at the Iconic Windsor Guildhall

Windsor

Join us in the historic Windsor Guildhall Chamber, surrounded by iconic royal portraits and seated beneath its magnificent chandeliers, for an unforgettable afternoon of opera with Rogue Opera.
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
Cookham Festival

Cookham, Maidenhead

The Cookham Festival is a celebration of the arts by the village, for the village with over 40 events taking place over the festival fortnight.
Symphonic ABBA

Windsor

The Thames Valley Festival Orchestra returns to Windsor Parish Church, High St, Windsor, Berkshire on May 2, 2026 to perform Louis Clark's 'Symphonic ABBA' arrangements. This follows performances of their highly popular programmes of 'An Evening of…
Windsor Jazz Club: Michael Wilkins Quartet

Alma Road, Windsor

Michael Wilkins Trained at Birmingham Conservatoire and Leeds College Of Music. He is a regular soloist at The Rose And Crown in Oxford, Goring Community Jazz Club, Ma Bessie's Pig Foot Band, as well as guest soloist at Windsor's Jazz Vanguard. He…
Elton John Tribute Night

Maidenhead

Get ready for a fun-packed, high-energy celebration of Elton John’s greatest hits! Absolutely Elton brings the magic of Sir Elton to the stage with vibrant showmanship and live piano for an authentic, unmistakable sound.
The Butterfly House

Ascot

This May experience a unique family theatre in the park. Follow the path into the woods at Tom Green's field, bring a picnic and a rug, and get cosy under the trees. "The Butterfly House" is a show that is inspired by nature and packed full of…
TripAdvisor Traveller Rating
1738 reviews
Allegra

Windsor

Allegra is a moving comedy with spectacular song and dance sequences, but is also a touching and emotional examination of how, sometimes, the most beautiful of minds can start to disappear.
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.
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.
Fi.Fest

Maidenhead

Experience Fi.Fest: a feel good family-friendly summer music festival in Fifield, perfectly placed between Windsor and Maidenhead in Berkshire. Join us on 10 and 11 July for two days of live music, food and fun for all ages.
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…
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.
TripAdvisor Traveller Rating
523 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.