Man who swapped rugby career for singing is cycling from Edinburgh to Glastonbury Festival ahead of his performance

A singer who swapped playing professional rugby for songwriting is now cycling 700 miles from Edinburgh to Glastonbury to celebrate landing his dream festival slot.

Jack Cullen, a 30-year-old singer-songwriter who lives in North West London, became a rugby player for Ireland and Munster under twenties after finishing school.

But in 2016, a series of injuries left him bedbound and, after picking up his guitar, he decided he wanted to make a career “U-turn” and pursue music.

He gradually began headlining gigs and, in May 2025, found out he’d secured a slot at Glastonbury Festival.

To make the most of the moment, he set off on a cycling trip from Edinburgh to the festival with his childhood friend George ‘GK’ Kershaw, 33, on May 30.

Their route has taken them through Newcastle, The Lake District, Manchester, Liverpool and Bristol, performing in quirky venues, including a sauna, and an intimate gig for one of his most loyal fans, along the way.

Jack is set to perform at the famous music festival on June 29 and hopes his best friend will be in the crowd – despite going on this “intense journey” with him, he does not have a ticket.

Jack told PA Real Life: “I have this fan who’s messaged me on a lot of occasions about how my music has helped him.

“He always drives from Liverpool to London to every one of my shows and that just blows my mind.

“So we…performed for him and we had some beers after, and to be honest, it’s probably one of the best little gigs that we’ve done so far along the trip.”

After finishing secondary school, Jack became a professional rugby player, going on to represent Ireland in the U20 World Cup and Six Nations.

In 2016, a series of injuries, such as damaging his shoulder and tearing his anterior cruciate ligament, left him bedbound, while also recovering from a breakup, and he picked up his guitar and began writing music, which he found “cathartic”.

Almost instantly, “the passion and love for music became too strong” to ignore, prompting a “complete U-turn” into a music career.

Over time, Jack began headlining tours across the UK and built a fanbase, now having over 20,000 followers on TikTok.

In May 2025, Jack was ecstatic to find out he had secured a Glastonbury slot and wanted to “make it a moment (he’ll) never forget”.

So, on May 30 2025 –  the day his new single All I Need was released – Jack and his best friend set off from Edinburgh on a 700-mile cycling trip to the festival, performing in small venues along the way.

Jack said there was “no training required”, as he was already physically fit, so the pair just packed up their bikes “and got on the road”.

His friend, George, known as the “head of logistics”, planned the route and embraced the challenge, despite not even having a ticket to the festival.

Jack joked: “We might be able to sneak him in in a guitar case! It just shows he’s the best person for the job and is here for the journey together.

“It’s an adventure…it’s all about meeting people and connecting via music and promoting the song, the journey, and having a good time whilst doing it.”

On their bikes, the pair have two pannier bags, a tent, food and waterproofs, and Jack has a large front bag with his guitar strapped on top.

“It’s not the most streamlined bike, we’re not going very fast anywhere,” Jack laughed.

“We also have two speakers on our bikes…so we often look and nod at each other and say, ‘It’s time’, and we put the tunes on when we need to dig deep or get up a big, big hill.”

The pair followed the east coast from Edinburgh to Newcastle, staying with Jack’s grandparents and making a pit stop on June 4 for his cousin’s wedding.

“I had my suit rolled up on the bike for the first week, which was really funny, unravelling the suit and then getting suited and booted for the wedding,” he added.

“We’ve been really flexible – the amount of miles we do just depends on the day.”

Next, they travelled to the Lake District, on June 5, where a team from London shot the music video for Jack’s first single with RCA Records, All I Need.

Jack said: “All I Need (was) written off the back of time spent away from home – it’s a moment of celebration as the noise of the outside world falls away to be reminded of what truly matters.”

Throughout the journey, Jack has also recorded sounds of nature, like birdsong, to incorporate into the acoustic version of All I Need, with 50% of the profits going to Earth Percent, the music industry’s climate foundation.

They then headed to Manchester, on June 10, where Jack performed in a sauna, which despite being “boiling” he “loved”, and afterwards travelled to Liverpool to play a gig for one of his most loyal fans.

Afterwards, they continued to Bunbury, Cheshire, performing in a friend’s cafe and later staying with some of George’s family, even playing a set in their living room.

Along the way, Jack has been documenting the journey on Instagram and TikTok under the handle @jackcullenmusic, hoping to “inspire others” to embark on similar adventures and further connect with fans.

Now in Bristol, Jack has “funnily enough” performed another gig in a sauna and also plans to perform for a local run club.

Jack and George aim to arrive at Glastonbury around June 25, where Jack is scheduled to perform on June 29 at 2:50pm on the Wishing Well Stage.

He said: “There’s going to be a whole new EP’s worth of music which people won’t have heard, which I’m very, very excited to almost debut at Glastonbury.

“They’re going to hear some old songs, but I think it’s going to be a whole big release of energy, and hopefully people will leave feeling really good.”

He believes this journey will shape his future songwriting – just as previous challenges, such as running 12 marathons in 12 days in August 2023, have inspired him.

After his Glastonbury set, he’s due to perform in Cornwall, but he will “probably have to skip cycling there” due to time constraints.

“I would if I could, but I will probably need a break at some point!” Jack said.

To stream Jack’s new single, visit: www.jackcullen.lnk.to/AllINeedPR.