The late Sir Woolf made it clear that an element of surprise would always be associated with the announcement of the awards and no applications were accepted.
More than 1100 principals and teachers from around New Zealand have received the award over nearly 60 years.
"It is a great honour, and something you don't expect ... to get something like this, I guess it's like winning Lotto," Walsh said.
In his element, Walsh would begin his journey at Harvard University for a week-long course among world education leaders.
From there, the focus of the trip would be around the best practice of learning support; particularly dyslexia, dysgraphia and autism.
"We have a large number of children at John Paul College who require learning support, and while we do an excellent job with them, it's always good to see how other schools and jurisdictions deal with learning support."
He would also travel to London and visit schools to learn about some of the leading practice in the realm of learning support.
Prague and Belgium were also on the itinerary.
But he also planned to admire the architecture and history of medieval Prague and looked forward to visiting his brother who lived in a castle in Belgium.
"I'm hoping to stay in the castle a little while," he said.
The grant allowed for the partner of the winner to join the trip, and Walsh said it was fitting his wife was the special needs co-ordinator at the school.
"It will be good for professional development for her as well," he said.
The Ministry of Education supported the award and would provide relief for Walsh which meant he would keep his salary.
The award was good for Rotorua, he said and showed the small city was up there with top Auckland schools.
Earlier this year, Walsh went on sabbatical, mainly around New Zealand, and wrote a paper on the benefits of different leadership modules.
