He was soon in partnership with a Mr Irvine, seeking contracts with Cook County Council.
In 1896 they gained a contract to provide metalling for Tatapouri Hill.
In the mid-1890s, Mr McCracken, with Tom Byrne and Tom Donavan, signed a contract to construct a road from the top of Waipiro hill, and to clear a track to Makarika.
The only other roads in the Waiapu County were from Waipiro Station to Takapau, about a mile (1.6km) on the Te Puia side of the Ihungia-Mata Road turn-off.
While engaged in various track- and road-making contracts in the Te Puia/Tokomaru Bay districts, he met, and in 1897 married, Henrietta Walter, who worked as a domestic at the Williams' homestead at Turihaua Station.
In 1898 McCracken built the first road from Te Puia Springs to Waipiro Bay, the sea port serving Waipiro Bay Station and surrounding holdings — Takapau, Ihungia, Puketoro, Puketiti, Pouturu, Te Pora, Owhena, Waitahaia and others.
A stellar reference from Waiapu county engineer George Winter set him up for continuous work for the rest of his contracting life.
He had earned a reputation for painstaking and capable work.
By 1900, he and Dan Malone had a Cook County contract to build eight miles (12.9km) of road eight feet (2.44 metres) wide north from Tolaga Bay along the Hikuwai River.
Further work followed on the track leading over the hill into Tokomaru Bay.
Mr McCracken and Joe Robinson brought the first wheeled vehicle to Te Puia Springs over a new road constructed in 1902.
Before this the track to Tokomaru Bay from Waipiro via Te Puia was over the Tawhiti Block, emerging at Waima and on to Tokomaru Bay along the beach.
With John O'Shea, he built the first main road in the Waiapu County Council area. It was three miles (4.8km) long, starting at the county boundary near Uawa and finishing at the first of the three Hikuwai bridges.
In 1903, the McCrackens moved to Te Puia Springs which was then a wilderness of manuka and fern and raupo swamps, with the only clearing being around the mineral springs.
They packed their possessions and the first two of their seven children on horseback and made the trip.
In 1905, McCracken levelled the site for the Te Puia Springs Hospital that was built the following year.
He built the jetty at Te Ariuru, using large manuka trunks for piles, and was building contractor for the Waima wharf, Tokomaru Bay, about a mile north. The original wharf was built in 1911-12 for £10,000, with an extension in 1914.
The McCracken-built bridge leading to the wharf celebrated its 100th anniversary last year.
A new wharf was built in 1940 at a cost of £28,300.
Bridges of that time were designed to carry horse traffic but many of McCracken's bridges survived into a time of transport weights unforeseen in their specifications.