Take a walk down Wellington’s most colourful street with The Spinoff’s Wellington editor Joel MacManus.

From the bucket fountain to the rainbow crossing, Cuba Street is home to culture and controversy. While it’s not that long – just 925m – each block offers a different flavour. Here’s what to explore and expect on each one.

Webb Street to Karo Drive 

This is the crunchy end of Cuba Street. If it were a person, it’d be your aunt with the flowy pants who smells like incense and loves yoga. Case in point: this is where you’ll find The Nut Store, a brick-and-mortar retail store that only sells bags of gourmet nuts and magazines about growing nuts. Somehow it has been running for well over a decade. Across the road, you’ll find Good Housekeeping, a sustainable homewares store. I’ve never bought anything there, but I like it because it smells nice. 

It’s always worth stopping in at Thistle Hall, a community gallery with a constantly rotating display of art exhibitions and classes. They offer yoga, knitting and dance classes and are also home to a guitar society. The last time I visited, two Irish Mammies tried to feed me pumpkin soup, which I think was some form of performance art. 

Treasures at Ziggurat, a vintage shop a bit further down (Image: Supplied)
Karo Drive to Abel Smith Street

As you cross Karo Drive, you enter Cuba Street’s chillout zone, a peaceful respite past the roar of State Highway 1 traffic, but before the busier high-foot-traffic areas. 

At Te Whare Manaaki o Toda, a community space associated with the Buddhist centre, you’ll find a contemporary art gallery with displays usually themed around Zen and inner peace. Over the road, Heyday Beer is one of the best spots in town to sip a cold one and relax on a sunny day. 

If you’re not in a rush, take your time perusing the Mary Potter Hospice Shop. Cuba Street is famous for its op shops. Mary Potter is the cheapest and has the widest selection. It’s a classic charity shop with classic charity shop prices, racks of clothes, books, knick-knacks and assorted things. It’s the kind of place where it’s easy to lose track of time. 

A vintage clothing store interior with racks of assorted jackets and shirts, a mannequin wearing a dark outfit, framed photos on brick walls, and a leather jacket and boombox displayed on shelves.Hunters & Collectors, one of the many vintage/op shops on Cuba Street (Image: Supplied)
Abel Smith Street to Vivian Street

The third block of Cuba Street is a foodie’s dream with a fantastic range of eateries from cheap street food spots to gourmet restaurants. If there’s one cuisine you have to try on any visit to Wellington, it’s Malaysian. Wellington has one of the strongest Malaysian food scenes outside the Asian continent. And that’s not just a personal reckon. To learn more about how Wellington became a cornucopia of Malaysian food, read this story by Preyanka Gothanayagi. On this block, you’ll find Satay Malaysia which topped The Spinoff’s ranking of Wellington’s roti canai combos. My favourite Malaysian spot for a sit-down dinner or small BYO is Rasa Malaysia (get the Murtabak).

A red wall decorated with a vintage bicycle adorned with baskets, hats, musical instruments, a sign reading "RASA," framed photos, and jars filled with spices.Rasa (Image: Supplied)

If you’re not in the mood for Malaysian food, consider Wellington Seamarket for the freshest fish and chips in the city, Nolita for creamy vegan pasta, El Matador for tapas and steak, Ombra for classic Italian – or for a bougie dinner on the corporate card, check out Logan Brown or Liberty. 

A person stands on a street corner outside Ombra, a restaurant in a light grey, three-story building with large windows and prominent signage, on a sunny day.Ombra (Image: Supplied)
Vivian Street to Ghuznee Street

On the corner of Vivian Street there are two benches dedicated to icons of Wellington’s Takatāpui Rainbow community, Chrissy Witoko and Carmen Rupe, who owned businesses and performed in clubs in this area when it was Wellington’s red light district. 

It’s a good idea to take a seat and rest your legs here, because there’s plenty of exploring to do on this block. This is where you’ll find the best range of second hand clothing stores: Frutti, Huha, Dandy Vintage, Perfect Circle, Ziggurat, Hunters & Collectors, Comrades, and my personal favourite, Spacesuit. 

A person stands inside a colorful record store, browsing shelves of vinyl records. The walls are covered with vibrant posters and album covers, creating a retro and eclectic atmosphere.Slow Boat Records (Image: Supplied)

Music lovers can take their time picking through the boxes at Slow Boat Records and explore Flying Nun Record Store for the latest releases from great Kiwi bands. In the evening, make sure to catch a gig at San Fran – even better if it’s someone you’ve never heard of before.

You’ll need some fuel for further thrifting, so make sure to check out Fred’s, the sandwich hotspot that always seems to have lines out the door. Get caffeinated at Midnight Espresso, or wet your whistle at the Cuba Street Tavern. 

A barista stands behind the counter at a cozy café called "Midnight Espresso," with pastries on display and a large menu with colorful chalk writing hanging on the wall behind them.Midnight Espresso (Image: Supplied)
Ghuznee Street to Dixon Street

When you think of Cuba Street, this is probably the bit that comes to mind. The main show. The pedestrian mall. My favourite thing to do on this block is to simply spend time on the street. Sit in the sun, watch the crowds go by, applaud a street performer, avoid the people handing out religious pamphlets, and weep at the majestic glory of the bucket fountain. 

The popularity of the pedestrian mall means some of the weirder shops have been priced out by chain stores, but there are plenty of interesting independent retailers. Check out Graphic for comic books and graphic novels, Wellington Apothecary for oils, candles and skincare, and Abstract Design for an eclectic selection of wall art and hanging decorations. 

A lively city street at dusk with colorful shops, a whimsical bucket fountain in the center, illuminated buildings, and a partly cloudy sky overhead. People are visible strolling along the sidewalks.The sometimes-bubbly bucket fountain (Image: Supplied)

Cuba Mall is an increasingly popular nightlife destination, particularly among punters who prefer a lively chat rather than a raging boogie down Courtenay Place. JJ Murphy & Co and Hotel Bristol are longstanding favourites for a classic pint and some pool. Loosies Superette, with its downstairs Saloon Bar, is a popular new hotspot. The Spinoff’s food columnist Nick Iles described The Ram as his “dream pub” and in-the-know locals flock to Dee’s Place, a tucked-away whiskey bar with no sign on the door. 

Left Bank 

A tributary tucked off to the side of Cuba Mall, Left Bank is a wondrous secret world which The Spinoff ranked as Wellington’s best laneway. Gritty but artsy, private but distinctly urban, Left Bank is my favourite part of Cuba Street. 

A cozy bookstore called Pegasus Books has bookshelves and carts filled with colorful books outside. Two people browse among the selections, and large windows reveal even more books inside the warm, inviting shop.Pegasus Books (Image: Supplied)

The real star of Left Bank is Pegasus Books, which topped yet another Spinoff ranking; Wellington’s best second-hand book stores. Pegasus Books is a work of mystery and mayhem, with an enormous trove of literature that spills out onto the street, shelves stacked so high that you need ladders to access half the books on offer, and a maze of a layout that seems to go on forever like a Tardis made of wood and paper. I stop in at Pegasus Books every time I’m in the area and end up buying something about 50% of the time. 

While you’re exploring Left Bank, it’s also worth checking out The Oatery, a cafe specialising in porridge and muesli. Cuba Street Social is possibly the coolest barbershop in Wellington, and I am absolutely obsessed with the Ethiopian cuisine at Mother of Coffee. 

Dixon Street to Manners Street

At Dixon Street, you’ll find Wellington’s rainbow crossing, installed in 2018 as a symbol of support to the city’s queer community – the green pedestrian crossing signal depicts Carmen Rupe strutting her stuff. Adjacent to the crossing is the aluminium sculpture Umbrella by Peter Kundycki. First installed on lower Cuba Street in 1990 and moved to this spot in 1997, it is a colourful reference to the city’s high rainfall that has taken on greater meaning to the queer community as a symbol of shelter and protection. 

This block is pretty short and the real action here is on Dixon Street, which has experienced a hospo resurgence thanks to a new boardwalk and parklets (on-street carparks that have been converted to outdoor seating with grass and trees). Swimsuit Coffee has a strong claim to the highly contested title of Wellington’s best coffee spot. 

A vibrant rainbow-colored crosswalk spans a busy city street lined with modern buildings. Pedestrians wait and cross under bright sunshine, with shops and a yellow-and-orange umbrella visible. Traffic lights are red.The rainbow crossing (Image: Supplied)
Manners Street to Wakefield Street

The standout businesses of Lower Cuba Street are not on the street itself but underground. Ivy Bar & Cabaret is a fun and fabulous queer bar where you can catch a drag show, a comedy gig, or dance the night away. Next door is R Bar, a fascinating underground rum bar that feels like a secret pirate lair, complete with skeletons, buried treasure and sea shanties. 

As you reach the end of Cuba Street, there’s an important but unmarked historical site. On the left side of the street, near the Philanthropist’s Stone sculpture, you’ll find Bond Street. Down this laneway was the original meeting house of the Dorian Society, New Zealand’s first homosexual organisation. Primarily a social club, it later formed a legal subcommittee that laid the groundwork for homosexual law reform in New Zealand. 

It’s a site that speaks to everything that makes Cuba Street special. This is a street that stands at the forefront of change, embraces differences, and encourages people to stand out.