Jack Cullen, a 30-year-old singer-songwriter based in North West London, has made an extraordinary transition from professional rugby to music, culminating in an inspiring journey to Glastonbury Festival. After representing Ireland and Munster under-20s in rugby, a series of injuries in 2016 forced Jack to reconsider his path. Bedbound and searching for purpose, he picked up a guitar and found a new passion in songwriting.
Since then, Jack has steadily built a thriving music career, headlining gigs and amassing a following of over 20,000 on TikTok. His breakthrough came in May 2025 when he secured a coveted slot at Glastonbury Festival, a dream come true. To mark the occasion, Jack and his childhood friend George ‘GK’ Kershaw, 33, embarked on an ambitious 700-mile cycling journey from Edinburgh to the festival grounds.
Setting off on May 30—the same day Jack released his new single, All I Need—the duo has taken a scenic route through iconic cities like Newcastle, the Lake District, Manchester, Liverpool, and Bristol. Along the way, Jack has performed intimate and often unconventional gigs, including a memorable sauna session and a private show for one of his most dedicated fans in Liverpool.
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Jack’s friend George, dubbed the “head of logistics,” carefully planned their route, embracing the challenge despite not having a festival ticket himself. Jack humorously suggested they might even sneak him in a guitar case, underscoring their close bond and shared adventure.
Their journey is as much about human connection as it is about music. Equipped with pannier bags, a tent, supplies, and Jack’s guitar, they navigate the road slowly but passionately. Music speakers mounted on their bikes help them power through tough climbs and keep spirits high.
The cycling trip has included meaningful stops, such as visiting Jack’s grandparents, attending his cousin’s wedding (with suit in tow), and filming a music video for All I Need in the Lake District. Jack explained that the song reflects a peaceful moment away from life’s noise, reminding listeners of what truly matters. He’s also been recording natural sounds like birdsong to enrich an acoustic version, with half of the track’s profits pledged to Earth Percent, a music industry climate foundation.
After performing in unique venues—including a friend’s café and intimate family living room sets—they arrived in Bristol. Here, Jack again delighted fans with a sauna performance and plans to entertain a local running group.
Jack and George expect to reach Glastonbury by June 25, with Jack scheduled to perform on June 29 at 2:50 p.m. on the Wishing Well Stage. His set promises a mix of beloved songs and fresh material from his upcoming EP, promising an uplifting, energetic experience for the crowd.
Reflecting on the journey, Jack said, “It’s an adventure about meeting people and connecting through music. This festival performance is a moment I’ll never forget—a celebration of the journey from rugby to this incredible new chapter.”