Isle of Wight Festival 2026: Day Two with Newton Faulkner, Anastacia, Rita Ora, Teddy Swims and Calvin Harris

Saturday at the Isle of Wight Festival is a demonstration of nostalgia, showmanship and pure fun. Marked by eras of fond familiarity, this line-up feels like a safe pair of hands, bringing together experienced household names such as Rick Astley, Anastacia, punk icons Sex Pistols and headliner Calvin Harris. Despite starting the day under a blanket of grey clouds and the threat of rain, the atmosphere is instantly brightened by the festival’s “Galactic Glamour” dress-up theme: the fields glow with the vibrant shimmer of sequins, wonderfully wacky outfits, before being greeted by the fashionably-late sunshine, setting the stage for another packed day and night of music.

Aside from the two main stages, there is a map full of other attractions and stages to explore. One of these is the charity-supporting Kashmir Cafe, a relaxing tent supporting local artists, which becomes host to folk-pop singer Newton Faulkner. It’s rare to see such an established artist on such a small stage, so the tent is unsurprisingly overflowing with festival-goers having spotted his name on the line-up; there’s a lot of heart in the guitar-slapping acoustic performance, and they are certainly not left disappointed.

Over on the Main Stage, Scottish singer KT Tunstall and Anastacia get the afternoon into full swing; the latter is unapologetically giddy to be here, and her powerhouse vocals delight the crowd with the signature hits but also a surprising turn of covers such as Sweet Child O’Mine. Pop nostalgia continues with shockingly in-sync boyband choreography from 5ive, followed by timeless baritone Rick Astley, proving that he’s much more than just one song, whilst also celebrating what has made him so popular throughout since 1987. It would be near-impossible to find one person in the crowd not singing along to Never Gonna Give You Up with a smile on their face. Next on, Rita Ora brings a high-energy pop spectacle, putting on a complete show as she takes the crowd “on a journey” through her career since 2012. One fan is even invited onto stage for a birthday song, amusingly resulting in the singer running out of time and asking the audience to choose her final song (Anywhere).

Whilst the billing is anchored by iconic throwbacks, it also shines a spotlight on newer talent. One newer face is Teddy Swims, delivering one of the standout sets of the entire weekend. Again, far more than his breakout song “Lose Control,” the soulful American singer balances genre-blending soul with a jaw-dropping vocal range. You’ve Got Another Thing Coming is highly animated, Are You Even Real showcases an amazing band dynamic and Some Things I’ll Never Know is beautifully stripped back. In between tracks, he’s also raw and emotional about how sharing his music and being vulnerable has saved his life. It’s also the elevated performances of his lesser-known material which make the greatest impact.

As the night settles, attendees gather for an open-air Saturday party: chart-topping DJ and producer Calvin Harris transforms the Isle of Wight into Ibiza, spinning non-stop dance anthems under a canopy of lasers and lights. Sure, the setlist is somewhat expected as one can guess exactly which hits will be featuring – and even the drops that will set off a frenzy of fireworks – but that doesn’t take away from the euphoria. Summer reminiscing can be found in poppier We Found Love, One Kiss and Summer, but admirably the final song is a tribute to Avicii with a cover of Levels. It’s a special moment, enough to set the whole crowd off and a perfect closer to this feel-good Saturday.