Festivals in the Windsor area

Here in the Royal Borough of Windsor and Maidenhead we are lucky to have very different types of events that fit under the 'festival' heading embracing not just literature, music and the arts but diversity, inclusivity, food and drink too!  Explore a wide range of festival events taking place in the Windsor and Maidenhead area.

Windsor Festival, 13-30 September 2025

Celebrating music, literature and the arts across two weeks, the Windsor Festival Autumn Festival is dedicated to delivering high-calibre performances in magnificent venues. 

Windsor Fringe Festival, 19 September-11 October 2025

Windsor Fringe offers a mixed programme of the arts and entertainment: music of all kinds, drama, visual arts (including photography and sculpture), film, poetry, informative walks in Windsor, gastronomy – and even conkers. Many young artists, such as soprano Dame Emma Kirkby and jazz musician Jamie Cullum, cut their teeth in the Fringe, and went on to become household names.

Ascot Beer Festival, image Nicole Hains

Ascot Beer Festival, 3-4 October 2025

Beer tastes best outdoors watching premium sport with friends and family and Ascot delivers this with pride as part of the BetMGM Ascot Autumn Racing Weekend. As one of the largest beer festivals in the South East, racegoers can enjoy the opportunity to sample their choice of over 160 different beers, lagers, real ales, ciders and perries. This rustic and traditional style CAMRA (campaign for Real Ale) beer festival, with a modern twist, has something for everyone.

Oktoberfest, Royal Windsor Racecourse, 10-11 October 2025

Get ready to raise your steins and stomp your boots, Oktoberfest has arrived in Windsor! Step into a world of Bavarian tradition and lively celebration; from toe-tapping music and hearty food to fun-filled games and festive attire, this is your chance to experience the charm and cheer of Germany’s most iconic festival - no passport required.

Cliveden Literary Festival

Cliveden Literary Festival, 11-12 October 2025

Evoke the spirit of the great writers and potentates who stayed here and continue the tradition of the house as a sanctuary for lovers of literature. Cliveden Literary Festival promises lively discussion, innovative ideas, and political debate, which reflects Cliveden’s own story.

Parallel Windsor, The Long Walk, image Ange Harper

Parallel Windsor | Festival of Inclusivity, 5 July 2026

Parallel Windsor is the UK's national celebration of disability inclusion and wellbeing.  This award-winning event is held in the grounds of the majestic Windsor Great Park and staged on the iconic Long Walk.  Parallel features a range of challenge events for everybody of all ages, health conditions and abilities so participants can 'start together, finish whenever'.  Parallel Windsor also features a fully accessible Festival of Inclusivity, providing lots of inclusive fun and entertainment for the whole family including a wonderful charity village, picnic area and yummy food concessions.  There is also a huge range of activities and entertainment - Live Music Stage, Arts and Crafts, Storytelling, Sport, Active Lifestyle, Play, Skills and Careers, Technology, Mobility and Community.

Fi.Fest, 10 & 11 July 2026

Fi.Fest is a family-friendly summer music festival event that takes place in Fifield, located between Windsor and Maidenhead in Berkshire.  It's an exciting weekend filled with amazing music and non-stop entertainment.  ​Start the weekend with the Fi.Fest Pre-Party on Friday. Enjoy great bands and DJs throughout the evening, along with fantastic food vendors and refreshing beverages to get you ready for the big day on Saturday.  ​Then brace yourself for an electrifying lineup of live bands and performers on our iconic main stage on Saturday. The KidsZone will be open all day to ensure all young Fi.Festers remain engaged, active, and creatively inspired.

TOTfest

TOTfest, 18 July 2026

TOTFest® Berkshire will take place at Royal Windsor Racecourse.  TOTFest® is the multi award-winning all inclusive festival entirely for children under 5!  It's a kid's festival with a BIG difference, TOTFest® is an entirely immersive event focused on igniting babies', toddlers' and pre-schoolers' imaginations. Catering for children aged 1-5, it's now the biggest under 5s festival in the UK.

Windsor and Eton Pride, 25 July 2026

Windsor and Eton's Pride event incorporates a parade on the Long Walk in Windsor Great Park followed by a festival of inclusivity in the centre of town.  The day is a joyful celebration of the contribution of LGBTQIA+ communities and individuals.

The Maidenhead Big Weekender, July 2026

The Maidenhead Big Weekender takes place at Braywick Sports Ground.  Get ready for two unforgettable days of live music, delicious food, exciting entertainment and summer vibes. Whether you're a music lover, a foodie, a thrill-seeker, or simply looking for a fantastic day out with family and friends, there’s something for everyone!

Rock the Rec, August 2026

Don't miss this annual celebration of music and community spirit!  Rock the Rec showcases a stellar lineup of acts bringing energy and vibes all day long.  Enjoy tasty treats; there'll be a variety of food stalls and a fully-stocked bar to keep you refreshed!  Explore unique handmade goods and support local artisans in the Craft Village.  Enjoy family fun: kids' crafting, a funfair, face painters and entertainment to delight the little ones.

Norden Farm Kite Festival, image Luminous Photography

Kite Festival, August/September 2026

Round off the summer holidays with this fun afternoon filled with kite making, food and drink stalls from local vendors, entertainment and, of course, kite flying.  Norden Farm's Kite Festival is an annual event and entry is free.

The Big Ascot Food & Wine Racing Weekend, September 2026

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, get involved with BBQ displays and marvel at live-cooking demos with Michelin-starred chefs. Live music and plenty of tasty food and drink options make this a memorable social event for all to enjoy!