Dens of sin and iniquity, hangings and humiliations - some of the city's most innocuous locations hide its darkest secrets.
The site of New Zealand's first execution
Corner of Queen and Victoria Streets
The drab exterior of the Queen Street ANZ belies the historical significance of the land on which it sits.
On this central city corner, 174 years ago, a young boy was preparing for his death.
It was March 7, 1842, and 17-year-old Maketū Wharetōtara was about to become the first person ever to be legally executed in New Zealand.
The gallows sat next to the Auckland courthouse and jail on the corner of Queen Street and Victoria Street West.
Wharetootara, the son of a Ngaapuhi chief, was sentenced to hang for a multiple homicide. He had been tried and found guilty of using an axe to split the heads of Thomas Bull, his wife Elizabeth Roberton, their two children, and their ward Isabella Brind as they slept at Motuarohia in the Bay of Islands. The adults were said to have abused him and offended his mana, but it was never understood why Maketu killed the children.
On the day of the hanging, Wharetōtara requested to be baptised. The ritual was conducted by Reverend John Churton, and Wharetōtara emerged Wiremu Kīngi
Maketū just hours before his death.
It was New Zealand's first state-sanctioned killing and far from its last. Between Wharetootara and Walter Bolton, who died by hanging at Mount Eden Prison in 1957, New Zealand executed 82 other people - 81 men and one woman.
Auckland Lunatic Asylum
Unitec, 139 Carrington Rd, Avondale
A warden run through with a pitchfork, a patient burned alive in a fiery act of revenge, a weeks' old body found hanging from the limbs of a willow tree - it can be hard to sort fact from fiction in the history of the Auckland Lunatic Asylum.
Built in 1865, the facility - known over the years as the Lunatic Asylum at the Whau, Avondale Lunatic Asylum and Carrington Psychiatric Hospital - was one of New Zealand's largest mental health facilities for nearly 130 years, until the building became Unitec in 1994. Now students study where Auckland's mentality infirm were once imprisoned.
Ghost stories abound, with tales of creaking doors and distant voices, faces at the windows and haunting music in the corridors - but tales of the supernatural pale in comparison to the real-life horrors of life at the asylum.
In the 1800s, the building housed around 1000 patients. Hundreds are said to have died at the hospital - both patients and staff - to suicide, fire and disease.
In 1922, 60 perished as typhoid ripped through the inmate population, aided by the facility's poor sanitation and hygiene conditions.
Some deaths are hard to confirm - is it true that a warden was murdered by a deranged patient with a pitchfork? In Building One, which now houses the architecture, design and contemporary arts departments, there is said to be a woman who stalks the corridors still, the victim of an 1877 fire which was lit by another patient and gutted the building.
On the other hand, the death of 35-year-old Thomas Meredith in 1897 was well covered in the press. After slipping away from his work in the gardens, staff and police undertook a search from Avondale to Henderson to find the escapee. It took them more than two weeks to locate Meredith, hanging by his belt from the branch of a willow tree just metres beyond the asylum walls.
The Bassett Road machine gun murders, 1963
Bassett Rd, Remuera
The headlines blared: 'Chicago comes to Auckland'. When the bodies of two grog-slingers were found bullet-ridden on the floor of a Remuera villa, the local press went to town.
Kevin Speight, 26, and George Walker, 38, were found dead by their landlord on December 7, 1963. They had been running their rented accommodation as a beerhouse, where boozers would disappear to continue the merriment once the pubs shut at 6pm, and the incident was assumed to be connected to this illegal activity.
The pair had been shot with a .45-calibre machine gun, and the papers painted a picture of a Chicago gangster-style turf war.
Career criminals Ron Jorgenson and John Gillies were arrested on New Year's Eve that year, and soon found guilty of the murders in a case so weak, some say would never make it through the courts today. Both received life sentences.
Following their release, the pair disappeared, and their whereabouts remain unknown.
Jorgenson's car was found at the bottom of a cliff near Kaikoura in 1984, amongst whispers that he had been executed, or faked his death and skipped the country. Gillies is said to be alive and kicking, living under an assumed identity in Wellington.
The bucolic gardens of Myers Park have long been known as a hotspot for seedy activity. Even these days, it isn't a place the average citizen would amble through after sunset.
Its grassy slopes and exotic trees are perfectly respectable now, but just over a century ago, this exotic leafy park was a pit of human wickedness and corruption - at least by the standards of the day.
Prostitutes and drug addicts, garbage piled high - this neglected gully was little more than a dumping ground for sewage and household scraps from the slums that backed onto the area, and the opium dens that surrounded it, servicing the newly established Chinese community living locally.
That all changed in 1915 when Arthur Myers - the founder of brewer Lion Nathan and Auckland mayor for more than a decade - gifted the park to the city, along with a GDP13,000 donation for its development and to build the kindergarden. Myer's Park became one of Auckland council's first beautification projects, a reform park intended to create a space for the children of the city's less fortunate residents.
Flora MacKenzie's brothel
Ring Tce, Ponsonby
It doesn't look much, this nondescript conversion on Pitt Street. But for more than 30 years, this rundown building housed Famous Flora's, a family-run brothel that was named after Flora MacKenzie, the infamous Auckland dressmaker turned Madam.
Flora's journey into brothel-keeping is fraught with rumour - did she turn her Vulcan Lane frock shop into a knocking shop, or was the first of her establishments in the block of flats her father bought for her at 17-19 Ring Tce, St Mary's Bay?
What is sure is that the enterprising Flora saw an opportunity in the American GIs who came to New Zealand in the 1940s, and set about servicing the serviceman market, turning her shop girls into working girls, and herself into New Zealand's most notorious Madam.
The Ring Terrace brothel was infamous and exclusive, occupying a large hillside villa with an uninterrupted view of the harbour, in the days before the Harbour Bridge had been built.
She was an entrepreneur and an eccentric, who kept Pekinese dogs and mixed her liquor with milk so she could sustain the drinking all day long. She was rumoured to have left her fortune to the man who delivered her weekly crate of whisky.
Whatever the truth, Flora was as famous in Auckland then as she is infamous now. She was a businesswoman and a feminist.
"I think men are useless bastards," she said, "running around crying because they need sex. I think the time will come when there are places for women to go for men. I think women should be able to choose the men, buy one, and then drop him afterward like they drop women."