Marking what would have been Richardson’s 85th birthday and 20 years since his death, the rally began in Christchurch on Thursday morning.
Drivers stayed overnight in Oamaru before continuing south, stopping at transport museums including Geraldine’s Roger Mahan Heritage Centre and the Kyle Park Heritage Museum in Timaru.
In Balclutha, the trucks paused at McLellan Freight’s Johnstone Rd depot for lunch and to view the late Alex McLennan’s collection of classic vehicles, before heading on to Invercargill for a parade based at Transport World, the museum founded by Mr Richardson in 2015.
"Most of the trucks and drivers here are working professionals, and there is a fair bit of competition between some of them," Bill Richardson’s grandson Harrison O'Donnell said.
"So for this many to be taking time off their commercial interests to get together for Bill shows the impression he made on a personal level."
Bill Richardson built on his own grandfather’s 1939 beginnings, growing his first venture, Southern Transport, into one of New Zealand’s largest family-owned companies, the HWR Group, now employing 2700 people over 40 businesses including in the fuel, transport, concrete and waste management sectors.
"It’s just to celebrate a great man," McLellan Freight owner Kim Unahi-McLellan said.
"Some wouldn’t be where they are today if it wasn’t for Bill ... He and Alex got on really well, they were both humble, down to earth people."
