The Sydney-based musician’s three finalist nods in the CMAA Country Music Awards of Australia include Album of the Year for his sixth album, Caught Up In The Dreaming; Male Artist of the Year; and Heritage Song of the Year with The Old Man’s Shed, a song written with longtime friend John Krsulja, from Nundle.

He’s preparing for a huge festival, with eight shows booked, including his regular gig at the Tamworth Services Club with his band, Medicine Wheel, as well as the Our Kind Of Country - A salute to Australian Country Music show at the Tamworth Town Hall and the Songwriters Retreat Showcase at The DAG Sheep Station, owned by Mr Krsulja.

O’Shea is one of the busiest established singer-songwriters during the annual festival, and after so many years gigging at the same spot, he’s created a huge fan following.

Tamworth is a chance to catch up with fans and fellow musicians.

“The services club has been integral to my development as an artist and Tamworth is really the highlight of my year,” he said.

“I get to play a whole series of shows with musicians that I respect and love, which is rare for us. 

“There's just not the budget now to take a band on the road.”

The latest album was inspired by several trips around Australia in an old caravan with his family.

The father of three is also a school teacher at Cronulla, but gets on the road as much as possible.

“We got meet some great Australian characters on the road and visit some amazing locations,” he said.

“We've got such a diverse country and each region is so distinct.”

O’Shea’s co-producer Benjy Pocock was among his biggest collaborators on the album, which was recorded at Pocock’s Queensland studio.

O’Shea also worked with industry peers and friends such as Amber Lawrence, Allan Caswell, Drew McAlister, Dana Hassall and Pete Denahy.

“When we were writing, and while recording, Benjy and I had a mantra of maximum joy, so it was a very fun process.”

He’s particularly proud of Old Man’s Shed, which could be O’Shea’s fourth song to win the heritage track award after The Drover’s Wife, Lady of the Land and Three Brothers (The Great War).

O’Shea and his friend and collaborator Amber Lawrence are also proud ambassadors for RSL DefenceCare, an organisation that helps current and ex-serving members of the Australian Defence Force and their families in times of injury, illness or crisis.

“The heritage award really means a lot to me, and Old Man’s Shed is very special to me,” O’Shea said.

“John and I are old school mates and we’ve had a wonderful 40-year friendship.

“We wrote Old Man’s Shed in honour of our dads, and I love performing that song, seeing the reaction from the audience before the song’s compete – tears flow, and laughter follows.

“I love seeing that range of emotion from the audience within the space of three minutes.”

He has a close connection to rural and regional Australia through his family roots and his work.

“It’s impossible for anyone who's toured this country not to have a real affinity with this place and I try to show that beauty through my music.

“That’s really what Joy McKean and Slim Dusty did – they were able to show how magnificent this country is through their words and song.”

While his family is based in Cronulla, close to the live music scene, O’Shea has strong ties to the Maules Creek area, where his father Rick was born.

His connection to that area led to his protest near the Leard Forest in January 2015, fresh from winning three Golden Guitars.

“I was fortunate to have the media spotlight for a small amount of time so thought, ‘let's shine it on the shadows and let people know what's happening’,” he saud.

“I couldn’t win Male Artist of the Year for the song Sing It Up, which is about farmers and everyday people fighting corporate greed, without doing something about it, so we locked on to a water pump.

“On the site that my father and I were arrested on, the house and shearing shed, built by grandfather and great grandfather, is now where a massive water pump with access to billions of litres of high security water sits.”

O’Shea said he was passionate about protecting Australian heritage.

“There are so many reasons why the huge Maules Creek mine shouldn’t have gone ahead, and the destruction of the forest is just one, but we’re also losing sacred sites of the Gomeroi.

“Sing It Up is a song about our actions and a call to farmers and activists to show them that they weren't alone, so my 71-year-old father and I locked onto a water pump.

“We had an overwhelmingly positive response from people across the country who understood why we were taking that action. We wanted to get people talking about what's happening in these communities.

“I feel a connection to the land through dad, and both sides of the family come from regional areas – Bathurst and Boggabri. And my backyard growing up was the Royal National Park, so I love the bush."

His three children are growing up with the same appreciation for rural Australia.

“They have a really great understanding of the size of this beautiful country.

“We do a lot of travelling with the kids in regional areas, so when I say I’m touring, they understand where I’m going.

“We just spent a few weeks on the south coast, where we disappear every year. There’s no reception and all we do is surf.

“We're completely in nature, exposed to the heat, thunderstorms, and wind. That makes you feel good for the rest of the year.”