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Welcome to the Royal Borough of Windsor and Maidenhead – a destination that knows how to celebrate! From lively music festivals and inspiring literary gatherings to cultural showcases, food and drink extravaganzas and family-friendly fun, there’s something for everyone. Whether you’re planning a day out or a short break, Windsor offers plenty of accommodation options for all budgets and countless things to do alongside our vibrant festival scene. Explore our Accommodation and Things to Do pages to plan your perfect visit.
Fi.Fest family music festival
Windsor’s music festivals are all about atmosphere, energy and unforgettable performances. Long Walk Live (26–27 June 2026) is a brand-new two-day celebration taking place near the world-famous Windsor Castle. Picture yourself on the iconic Long Walk, picnic basket in hand, enjoying live bands, tribute acts and local talent as the sun sets. It’s the perfect excuse to book an overnight stay and make a weekend of it. Another highlight is Fi.Fest (10–11 July 2026), a family-friendly music festival in Fifield. Expect an electrifying lineup, a buzzing KidsZone, and plenty of food and drink stalls. For those who love community vibes, Rock the Rec in August brings local acts, craft stalls, and family fun to Windsor. These events are ideal for music lovers looking for a mix of big-stage performances and grassroots talent. Double the excitement by planning extra time to explore Windsor’s attractions and enjoy local dining options.
Cliveden Literary Festival
If you’re passionate about books and ideas, Windsor’s literary festivals will inspire you. The Cliveden Literary Festival (October 2026) is a must-visit for thought-provoking discussions and debates in a historic setting. Meanwhile, Windsor Festival (12 September–3 October 2026) combines music, literature and the arts in stunning venues across the town. These events are perfect for culture seekers planning a relaxing short break with plenty of intellectual stimulation. Extend your visit to explore Windsor Castle and enjoy charming cafés that complement your literary journey.
Parallel Windsor, The Long Walk, image Ange Harper
Celebrate diversity and creativity at Windsor’s cultural festivals. Parallel Windsor (5 July 2026) is the UK’s national celebration of disability inclusion and wellbeing, featuring challenge events and an accessible Festival of Inclusivity. Windsor Fringe Festival (September/October 2026) offers a rich mix of music, drama and visual arts making it one of the most eclectic events in the borough. Don’t miss Windsor and Eton Pride (25 July 2026), a joyful celebration of LGBTQIA+ communities with a vibrant parade and town-centre festivities. These festivals showcase Windsor’s inclusive spirit and cultural richness, making them perfect for visitors seeking authentic experiences.
Ascot Beer Festival, image Nicole Hains
Foodies will love Windsor’s culinary celebrations. The Big Ascot Food & Wine Racing Weekend (4–5 September 2026) pairs gourmet delights with thrilling horse racing. Enjoy live cooking demos, Michelin-starred chefs and plenty of tasting opportunities. Beer enthusiasts should head to the Ascot Beer Festival (2–3 October 2026), one of the largest in the South East, offering over 160 beers, ales, ciders and perries. These events are perfect for those who want to combine great food and drink with entertainment and socialising. Extend your stay to sample local restaurants and enjoy Windsor’s vibrant food scene.
Norden Farm Kite Festival, image Luminous Photography
Families are spoilt for choice with Windsor’s kid-focused festivals. TOTFest® Berkshire (18 July 2026) is the UK’s biggest festival for under-fives, packed with immersive activities to spark young imaginations. Norden Farm's Kite Festival (August/September 2026) at Boyn Hill in Maidenhead is another favourite, offering free entry and a fun afternoon of kite-making and flying. These events are ideal for creating magical memories with little ones. Make it a weekend adventure by booking family-friendly accommodation and exploring Windsor’s parks and attractions.
Why not turn your festival visit into a short break? Windsor offers a wide range of accommodation, from luxury hotels to welcoming guest accommodation. Combine your festival experience with exploring iconic attractions like Windsor Castle, scenic walks in Windsor Great Park, and plenty of things to do for all ages. Check our Accommodation and Events Calendar to plan your perfect trip.
Number of results: 14
Maidenhead
Lunar New Year celebrations kick off in style on Saturday 21 February with the return of the much-loved Lion Dance Parade. Mark the Year of the Fire Horse as lions truly come alive on Maidenhead High Street.
Ascot
See the Jumps season out in style at Ascot’s Spring Family Raceday – our springtime extravaganza, where racing favourites meet family favourites.
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.
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.
Windsor
Parallel Windsor is the UK's national celebration of disability inclusion and wellbeing. Our award-winning event is held in the grounds of the majestic Windsor Great Park and staged on the iconic Long Walk.
Ascot
With the Flat season in full bloom, the Racing to Zero Summer Mile Weekend is a celebration of speed, skill, sun-kissed days and sustainability. Throughout the racecourse, you’ll find vibrant community and environmental showcases as part of our…
Maidenhead
Fi.Fest is a family-friendly summer music festival event that takes place in Fifield, located between Windsor and Maidenhead in Berkshire. Join us on July 10th and 11th for an exciting weekend filled with amazing music and non-stop entertainment.
Windsor
TOTFest® Berkshire will take place at Royal Windsor Racecourse on Saturday 18 July 2026. TOTFest® is the multi award-winning all inclusive festival entirely for children under 5!
Ascot
With the exception of Royal Ascot, King George weekend is the most important, historic and glamorous racing meeting on Ascot's calendar.
Windsor
Since the first Pride March in London over 50 years ago, the ever increasing number of Pride events have become joyful celebrations of the contribution of LGBTQIA+ communities and individuals across the UK. With our second parade taking place in…
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…
Ascot
The Big Ascot Food & Wine Racing Weekend offers a taste sensation alongside two days of fantastic late summer Flat racing. Peruse a range of food stalls and marvel at live-cooking demos with Michelin-starred chefs. Plenty of tasty food and drink…
Windsor
Each year the world’s finest musicians, writers, artists, and local performers entertain and delight festival audiences, celebrate Windsor's special place as a Royal town, and to inspire the next generation of artistic talent and creativity.
Ascot
Experience the perfect pairing of world-class racing and craft beer at Ascot’s Autumn Racing Weekend & Beer Festival, held in association with CAMRA (Campaign for Real Ale). This two-day celebration combines thrilling Flat racing with an incredible…
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