The "Aotearoa New Zealand History in the Making" expedition was first conceived in 1998, tentatively planned since 2005 and Mr Wilson calculates it could generate the equivalent of about $250,000 worth of publicity for Oamaru's Victorian Precinct.
There is also a personal challenge - covering more than 2000km on an 1880s-style, 54in high-wheeled penny farthing manufactured in Oamaru.
With its high centre of gravity, solid rubber tyres, fixed pedals and primitive "spoon" brake, he will have to pedal it over all sorts of terrain and in all kinds of weather.
The ride will start tomorrow as part of the Southern Most Ordinary Tour of penny farthings and veteran cycles to Oamaru for next week's Victorian heritage celebrations and penny farthing championships.
After stopping in Oamaru for a few days after the celebrations, Mr Wilson will be on the road again and expects it will take until some time in January to the finish at Cape Reinga.
There have been other epic tours of New Zealand by penny farthings, Mr Wilson said.
One was in 1884 from Auckland to Wellington by J. Fitton on a 52in penny farthing, at a time when roads were few.
Another was in 2007 when English wheelman Joff Summerfield rode from Invercargill to Auckland on his penny farthing.
Mr Wilson is captain of the Oamaru Ordinary Cycle Club. His expedition is believed to be the first recorded covering the full length of New Zealand from Bluff to Cape Reinga.
He will be travelling alone wearing the breeches and knee-high socks of the 1880-era cyclist, relying on his own resources, along with the kindness of strangers for comfort along the way.
He is also appealing for donations to help with the trip.
"It will require surviving such modern hazards as bad weather, hunger, thirst, stray animals, poor roads and encounters with inconsiderate and menacing motorists," he said.
He will keep a log blog of the trip at the end of each day's ride and anticipates generating publicity through interviews with news media.
