Festivals in Windsor and Maidenhead

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

Music Festivals

Windsor’s music festivals are all about atmosphere, energy and unforgettable performances. Long Walk Live (2027 dates tbc) is a two-day celebration that takes 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 (9–10 July 2027), a family-friendly music festival in Fifield. Expect an electrifying lineup, a buzzing KidsZone, and plenty of food and drink stalls. Maidenhead Big Weekender offers two unforgettable days of live music, delicious food, exciting entertainment and summer vibes. For those who love community vibes, Rock the Rec (30 August 2026) 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

Literary Festivals

If you’re passionate about books and ideas, Windsor’s literary festivals will inspire you. The Cliveden Literary Festival (10–11 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

Cultural Festivals

Celebrate diversity and creativity at Windsor’s cultural festivals. Parallel Windsor (11 July 2027) 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 (31 July 2027), 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

Food & Drink Festivals

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

Family-Friendly Festivals

Families are spoilt for choice with Windsor’s kid-focused festivals. TOTFest® Berkshire (July 2027 tbc) is the UK’s biggest festival for under-fives, packed with immersive activities to spark young imaginations. Norden Farm's Kite Festival (30 August 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.