The Mount Maunganui man has already skateboarded more than 2500km and has stopped off in the Bay of Plenty on his way to the top of the North Island.
Benefield is taking on the massive physical challenge to raise awareness about mental illness.
"It's been an incredible experience," Benefield says standing outside of Tauranga Intermediate.
When the 33-year-old left for Stewart Island in February he did not have a set plan of where he was going to go.
Instead, Benefield has gone where the wind has blown him; visiting different towns, schools, old friends and making new ones while sharing his story along the way.
"I've travelled to areas where I can make the most impact," he says.
On the days he is on the road, Benefield will skate between 30-50km with the longest journey clocking up 70km.
The road has not always been smooth for Benefield, which is why he started the campaign in the first place.
Four years ago he was medically discharged from the New Zealand Army - Royal New Zealand Infantry Regiment - after suffering from post-traumatic stress disorder and severe depression.
Adjusting to life after the military was a struggle and, he says, last year was one of the darkest times in his life when he was deep into depression.
"I love skateboarding, surfing and all board sports, so I thought why not set this challenge for myself?"
Speaking to a packed hall of Tauranga Intermediate School students, Benefield shared his personal story of the struggles he had experienced and his tales of the skateboarding journey.
"People keep asking me what the highlight has been and I can't put it down to one experience, but I can put it down to one word- connection," Benefield says.
"I've been able to connect with the land, the people and our youth."
Get involved with Ride Against Depression
-Blair is raising funds for No Duff Charitable Trust, Youthline and Good Neighbour Trust. To donate to his campaign visit- https://givealittle.co.nz/fundraiser/ride-against-depression-rad
-There is a Ride Against Depression auction evening to raise funds for the campaign on July 7 at Imbibe in Mount Maunganui from 5pm
-Get RAD merchandise is available at Relentless in Mount Maunganui or online, and 10 per cent of the proceeds go the charities Blair is fundraising for