And while Mr Brassett has worn out two pairs of shoes, Piccolo and Jake are padding along on healthy paws.
"Jake walks most of the time and I kept an eye on his paws early on, but they've toughened up now," he said.
Piccolo, a rescue dog, is much older and quite nervous and finds comfort inside Mr Brassett's sleeping trailer he hauls along behind him.
Powered by solar panels and weighing 100kg, but feeling like 150kg when heading up hills, the trailer can hold a 10-day supply of food, with 11 litres of water also on board.
Heading into winter there have been some icy moments, especially at Mangatinoka (between Woodville and Pahiatua) when the outside of his trailer was iced up.
"I was relatively cosy inside with the dogs," Mr Brassett said.
In the Tararua he's received typical country hospitality.
"On Sunday in Woodville I was heading to the camping ground when Dot and Dave Johnstone asked me to park up on their lawn.
"They then took me to their daughter's for a Mother's Day dinner. In Dannevirke I stayed at Murray Cushing's on Monday and Tuesday night."
His former job as a dog handler and trainer in Melbourne opened his eyes to the rough time some animals have.
"I often felt like the ambulance at the bottom of the cliff," he said.
"I'm now fighting for the animals who can't speak for themselves.
"I'm asking people to donate to my Givealittle page, not for me, but for the SPCA and animal-welfare groups.
"I'm living on less than $100 a week and am self-funded because I've saved enough money to live frugally.
"I've learnt you don't need much and the less you've got the better life is."
Another advantage of walking the length of New Zealand was discovering places he might like to live, Mr Brassett said.
"I meet people and get a feel for places."