Mr Dingle, who co-founded The Foundation for Youth Development (FYD) in 1995, teamed up with adventurer and businessman Jamie Fitzgerald to create the Big Walk event.
Their aim is to engage young people while also creating public awareness of youth problems such as suicide, unplanned pregnancy and drug and alcohol use.
The Big Walk was launched on November 30, with Mr Fitzgerald starting at Cape Reinga and Mr Dingle leaving from in Bluff.
They plan to meet in Wellington on February 1 for an event at Parliament, after achieving 3000km of walking between them.
Along the way, each walker will both be joined by groups of youngsters who have participated in foundation projects.
The young walkers will tackle segments of up to 100km each over four to five days.
The route for the next leg of the South Island part of the journey, which starts today, winds from Arrowtown to Twizel, via Lake Hawea.
Mr Dingle will be joined by a group of youths from Christchurch, who will be doing part of their journeys on mountain bikes.
After his first 450km Mr Dingle told the Otago Daily Times he had been impressed with the young walkers.
"Not only did they cope with cold and wet weather at part of the trip, some of them also took the initiative to do volunteer work along the way.
They asked Southland locals if they could do anything to help, and have been chopping wood and acting as farm hands.
"It was encouraging to see . . . the youngsters approach strangers and then feel they were giving something back to the communities they passed through.
"This is the kind of thing which could help to change people's perception of teenagers, and in turn make them more likely to help our young," he said.
As an important symbolic part of the project, a "po rongo" or "peace stick" is carried as a baton from group to group, giving the young participants a sense of continuity.
The teenagers, aged between 16 and 19, also write on a scroll, which is being carried to Wellington.
