Look for the long stretch of ridge-top road lined with heritage brick buildings and distinctive iron awnings that shelter the eclectic shopfronts below.
You are standing on the oldest thoroughfare in the city. Before European surveyors arrived, this ridge was a walking track used by Māori travelers. It carries the name Karangahape, which comes from a legend about a priest named Hape. The story goes that Hape was left behind in the Polynesian homeland because he had a club foot, which his people saw as a bad omen. He refused to stay put. He prayed for assistance and was picked up by a giant stingray, which delivered him here to this ridge before his people’s canoes even arrived. When they finally sailed into the harbour, Hape was standing right here, calling out to them. That call, or karanga, gave the ridge its name: Karanga-a-Hape.
For the first half of the 20th century, this wasn't just a road; it was the "Great White Way." In 1935, the city installed electric lighting under all these shop awnings, creating a mile-long tunnel of light for late-night shopping. It was the glamour mile, packed with department stores, tea rooms, and cinemas. But glamour has a way of fading when the economy crashes.
In 1932, during the Great Depression, a riot surged up from Queen Street. It was a raw explosion of frustration from the unemployed. Windows were smashed along this entire strip. The looting was... well, opportunistic. Looters grabbed whatever they could carry, leaving the street looking like a war zone as shopkeepers struggled to defend their property. The police were overwhelmed, and shopkeepers had to defend their shattered windows with whatever they could find.
The real blow to the area, however, came in the 1960s. Urban planners decided to build a massive motorway system through the nearby gully. To do it, they displaced fifty thousand residents who were the local customer base. They even dug up over four thousand bodies from the Symonds Street Cemetery. It was described by critics as archaeology by bulldozer.
With the shoppers gone, rents collapsed, and the red-light district moved in. This era gave rise to characters like Rainton Hastie, the self-proclaimed "King of the G-String." He ran the Pink Pussycat Club just down the road and was a master of shameless publicity. He drove a fleet of pink Cadillacs around Auckland to advertise his club. He even did time in prison for a show that exposed a little more than the law allowed back then.
Today, that gritty reputation lingers, but the reality has shifted again. It is now the bohemian heart of Auckland, a mix of artists, vibrant queer culture, and heritage architecture. It has survived riots, bulldozers, and pink Cadillacs to remain the city's most interesting ridge.
Take a moment to look down the street and imagine those pink Cadillacs cruising by. When you are ready to move on, we can head to the next stop.
