Some cities think they are cooler than they are, and some are cooler than they know. We’re not talking about literally coolness, either - though Hobart and Canberra do actually rank pretty high here.

    • Parking can be a problem near the coolest streets - it depends on the city
    • Make sure you’re hungry - food is a central theme for coolness
    • Impulse buys are common - art, shopping and cultural hot-spots offer heaps!

    We wanted to tell you about some of the coolest streets in the country - places where you can go to have a coffee, have dinner or a drink (or both), or just grab some shots to share on your socials.

    And while some of these are based on local knowledge, others are officially cool. Australia’s coolest street - according to the culture bible, TimeOut magazine - is also the second coolest street on the planet.

    Melbourne - Gertrude Street, Fitzroy

    Some way from the iconic graffiti-art alleys and crowded inner-city laneways, Gertrude Street in the inner-northern suburb of Fitzroy is known for its laid back vibe, artsy feel and Insta-worthy streetscape.

    With eye-catching murals, big glass store frontages, cosy bars, restaurants and cafes with outdoor seating, and shops and art galleries that allow you to take a little bit of Gertrude home with you, you won’t forget your trip down this 1-kilometre stretch anytime soon.

    It’s oh-so Melbourne, but also very much its own enclave.

    Sydney - Enmore Road, Enmore

    If you like your streets to have a slightly more grungy, alternative vibe, then Enmore Road will be your go-to hangout spot. We won’t get into the territorial boundaries, because you could think of Enmore Road as being in Newtown or Enmore, but either way, this busy stretch has street parking or a maze of back streets with timed zones. Just don’t lose your car, because those side streets can be confusing!

    It’s just a hop, skip and jump away from King Street, Newtown - AKA the other fork of the road - and it has an eclectic mix of shops, restaurants and bars, plus it’s the home of the cultural hub that is the Enmore Theatre.

    From the cheap and cheerful bakery to the Turkish ice creamery, to the Pakistani restaurant and a choice of different pubs, it’s a must for anyone who wants a taste of the real inner-west of Sydney. Expect students, and don’t be surprised if things get weird.

    Canberra - Lonsdale Street, Braddon

    Almost smack bang in the middle of the Civic CBD area of Canberra is a place where you will find many a public servant after hours, either snacking, drinking or shopping for a new pushbike. That’s because this hipster hang is home to breweries, bars, bike shops and bakeries alike. It’s a cultural hub for Canberra, and a great place to check out what is considered to be cool in the Capital.

    You might want to aim to be there around Autumn if you’re a fan of crunching leaves underfoot, but just be aware that in the middle of the year, this is a cold, cold part of town!

    This area used to be pretty rundown, but it has gentrified (and continues to) over the past decade. A tip - there is heaps of parking nearby, too, and if you see enough of the few blocks around Lonsdale Street, the Canberra Centre shopping mall is just a few hundred metres away.

    Brisbane - James Street, Fortitude Valley

    From high-end hotels to artisan bakeries, there’s a great mix of cool and contemporary stuff to check out on James Street, Fortitude Valley.

    You will be able to eat, sleep, drink, dance, walk and shop to your heart’s content, or just hang out under the overhanging fig trees and watch the world go by. Just don’t park your car under them for too long…

    For a pretty short strip of road there are dozens of restaurants and cafes to choose from, and you’ll want to keep a tally of how many high-end luxury cars you spot on the street. It’s a hangout for those who can afford to spend money on nice things, and nice cars are no exception.

    Perth - William Street, Northbridge

    It can be a bit quiet during daylight hours, but William Street in Northbridge in the guts of downtown Perth is a top spot to check out some of the city’s best (and affordable) eateries and bars.

    You will have your choice of a mix of different cuisines, and there are plenty of cultural experiences available along this strip of shops. Divert from this stretch of road and you will find a number of sneaky side streets with clubs, pubs, and places to stay.

    And just around the corner you’ll find the Art Gallery of Western Australia and the WA Museum Boola Bardip, too. There’s a lot to like about this part of town.

    Adelaide - Queen Street and Elizabeth Street, Croydon

    A hot spot for locals, this little treasure trove is perhaps an unexpected choice. It isn’t in the CBD, and out-of-towners might never know about it - but that’s what makes it cool.

    This small tree-lined street has mix of great food, wine, coffee and shopping spots, with vintage stores, art galleries and - amazingly - you can usually find parking in the area, if not on the street itself.

    It mightn’t be an audacious pick, but it is a lovely, if quiet, spot to soak up some of Adelaide’s finest fare, and there are more than a few Insta-worthy photo opps on the block, too.

    Darwin - Mitchell Street, Darwin

    A tourist enclave with a number of hotels and places to get a meal, Mitchell Street in Darwin’s CBD is also a great starting point to explore the laneways around the city area.

    Check out Shadforth Lane, Austin Lane and West Lane for some amazing full-scale murals on buildings, all part of the city’s push to liven up its image and get people seeing more than just their hotel room.

    There are heaps of places to get a cool drink (you’ll need one if you go wandering!), and within walking distance there’s also Bicentennial Park and Lameroo Beach, which make for a nice spot to get some shade or sun, depending on your preference.

    Hobart - Salamanca Place, Hobart

    It’s an oldie (literally) but a goodie. Salamanca Place is home to some heritage buildings, but it has heaps of new-world appeal thanks to a generous dose of cool places to go, sit, eat or sleep.

    You won’t find a park when the markets are on, but otherwise there are plenty of spots for your car. You might even get a prize position in front of a sandstone shop front for the ‘gram.

    This cool spot can literally be quite cold, so rug up - but many of the outdoor eating spaces have heating, and there are cosy nooks inside plenty of the street’s eating spots, as well. You could spend a week here and still not try every different spot - it’s that packed with places to choose from.

    Matt Campbell
    Matt Campbell is a Senior Contributor at CarExpert.