To provide you with the best experience, cookies are used on this site. Find out more here.

Follow Us...

La Bouche Manouche featuring Irene Serra

You are here: Home > Things to Do > Entertainment

Accommodation Search

Things to Do Search

What's On Search

Food & Drink Search

Shopping Search

Accommodation Search

Things to Do Search

What's On Search

Food & Drink Search

Shopping Search

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.

Number of results:

Number of results: 33

, currently showing 1 to 20.

Sort By: A-Z Lowest A-Z Highest

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
1742 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
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.
External Links
- Click here for your AccessAble Access Guide
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.
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.
Les Miserables

Eton

Les Miserables, the world’s longest running musical, is playing this July at the Farrer Theatre, Eton College. Come and be wowed by a cast of 90 Windsor Upper Schools students, with full orchestra, professional costumes and sensational set at the…
Summer Piano Series (2 of 4): Sherri Lun

Maidenhead

Sherri Lun, winner of the 2024 Birmingham International Piano Competition, performs in Maidenhead this July.
Reg Meuross - Fire and Dust: Woody Guthrie Story

Maidenhead

Commissioned and produced by Pete Townshend and created by award-winning singer-songwriter - Reg Meuross - Fire and Dust: Woody Guthrie Story is at Norden Farm Centre for the Arts on Friday 10 July at 8pm. Tickets are £23.
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.
Matt Forde: Defying Calamity

Maidenhead

Leading political comedian Matt Forde returns to Maidenhead on his biggest live tour to date – following a sold-out performance in May.
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…
Johnny Cash Roadshow

Maidenhead

Step into the raw and gritty world of Johnny Cash’s prison era with an electrifying show that has captivated audiences for two decades.
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.
Derick Clapton and the Dynamos, Eric Clapton Tribute Band

Maidenhead

From the fire of Cream to the soul of the Dominos and the enduring hits of the solo years, Derick Clapton and the Dynamos are the definitive Eric Clapton tribute.
Windsor Jazz Club: Debby Bracknell & Stuart Henderson

Alma Road, Windsor

A beautiful musical pairing of international star vocalist Debby Bracknell and melodic trumpet maestro Stuart Henderson. Tonight singing and playing a selection of favourite jazz.
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
The Maidenhead Big Weekender

Maidenhead

Get down to Braywick Sports Ground for the 2026 Maidenhead Big Weekender! Join us on Saturday 25th & Sunday 26th July for two unforgettable days of live music, delicious food, exciting entertainment and summer vibes.
Concertini with The Brass Funkeys

Maidenhead

This summer, The Brass Funkeys return to Norden Farm with their trademark high-energy brass spectacular. Expect everything from soulful jazz funeral marches, reggae, gypsy and swing to pumping brass-driven funk. Be inspired by sizzling saxes,…