On arrival in New Zealand, his first employment was on the roads from Lower Hutt to Waiwetu [Waiwhetu]. He worked on a small farm near the Hutt Bridge for Mrs Bircham. He moved up to Central Hawke’s Bay and managed Purvis Russell’s Woburn run until 1859 and later went to work for on Mr Thomas Lowry’s Okawa run for a year.
In 1867 John leased a run of 1100 acres at Puketapu from Karaitiana and soon turned his lease into a freehold title. He bought the freehold through R D Maney at an agreed price of £1,260. This was settled, not in money, but in payment of accounts. Paoro, the main owner, claimed that, for the land he received only shirts, trousers, blankets, sugar, 4 boxes of gin, 3 cases of brandy, 3 cases of pale brandy and £36 in money. He acquired other blocks in the district and built up a very large estate.
Te Kooti once worked for him and was in charge of men draining the property.
In 1860 the district was in the throes of the Maori War and camps were built and redoubts formed at Waipawa and Hampden. In 1863 when the war in the Waikato was in progress, John took up a contract for the cartage of camping gear. The river beds were the roads in those days and the [to] reach Peka Peka (Risssington) the river Tutaekuri and Mangahana [Mangaohane] had to be crossed 14 times, which to get to the old Tunanui station, the river had to be crossed 40 or 50 times.
John and Jane lived at the bottom of the Puketapu pa site which is the first hill on the right as you turn into Springfield road from Puketapu Rd. The foundations of the house can be seen, it burned down.
In 1866 the Battle of Omaranui [Omarunui] happened across the river and family legend tells of Jane (his second wife) hiding the younger children under the riverbank while the battle raged on above. This battle only lasted 1 day and a memorial commemorating this is in Omaranui Road, ironically just down from the homestead that son William bought later.
In 21st October 1863 John Heslop submitted a first notice in the Hawke’s Bay Herald advising the proposal of an establishment of a school in the Puketapu neighbourhood. He was on the first School Committee. He promises the land for Puketapu School. In 1864 the land is purchased from John Heslop. In 1880 he signs a 99 year lease with the Board for the school site.
Johns twin sons, George and William, took a lease on Chesterhope. The land area then was around 1440 acres. John snr began to farm cattle on the property in the 1870’s. John jnr began breeding racehorses. William was living in the homestead, parts of which apparently still remain in the present homestead, from about the mid-1870s.
In 1881, George bought William’s share of Chesterhope for 15,000 (2017: $2.478 million). During 1882 horse trainer, J R Jones leased stables at Chesterhope to train racehorses. That year the nearby Tutaekuri and Ngaruroro Rivers flooded Chesterhope. The flood caught out George Heslop and shepherd Martin O’Shanessy [O’Shaughnessy?] on their horses in a creek, and both fell into