Before the main event, Skilton said the schoolchildren and parents gained sponsorship from friends, family or colleagues, which will be donated to the trust.
"It was all about the community coming together for a cause that is very close to our school community."
While total funds were yet to be counted, Skilton said the event was a "huge success" with many parents, staff and Rieger himself joining in on a few laps.
Skilton said the children were educated about the Rieger family's story and the Spirit of Adventure before the event.
"As tragic as the story is it is important that people know what has happened and turning it into a positive," he said.
Since losing his son, it has been Rieger's mission to send as many teens, aged 16 to 18, on the three-masted barquentine commissioned in 1986.
On board, trainees take part in land and water-based activities including learning to sail the luggers, beach cleaning, tramping trips ashore, hoisting and setting very large and heavy sails, as well as opportunities to run the ship.
Although the event was not a surprise for Rieger, he still admitted being overcome with emotion.
"I was seriously in awe, what Matt and the team did was amazing. I did not know what to say," he said.
"It floored me. It was extremely emotional. I was blown away by the support and generosity."
To support the I Ride With Hame fundraiser, donate directly to ASB 12-3011-0461607-52. All funds go towards the Spirit of Adventure Trust.