Brimming with independent boutiques, galleries, bars and restaurants that channel a strong creative spirit, this storied street in Melbourne’s oldest suburb embodies what makes the city such a compelling place to explore.

You can trace the history of Melbourne’s oldest suburb through the story of Gertrude Street, which stretches through Fitzroy for one kilometre. Today it is a microcosm of all that is exciting about this inner-north enclave, with its kaleidoscope of businesses united by a fiercely independent creative spirit.

Gertrude Street was first developed on the land of the Wurundjiri people in the 1850s as a respectable residential and commercial precinct wrought in timber, bluestone, iron and brick thanks to the gold rush building boom. By the 1860s its range of shops and businesses included bakers, butchers, bootmakers, drapers, tailors, grocers and wine merchants, as well as a number of printers, saddlers and stores known as ‘fancy repositories’ selling everything from embroidery wools to wax flowers. But the street fell on hard times during the Depression of the 1890s, when the seeds of an infamous reputation that would last for decades would be sown: its 14 hotels operating along its length attracting characters of ill-repute.

Like Fitzroy itself, by the end of the First World War it was an area synonymous with trouble. But its spirit never waned. Post-Second World War migration enlivened the area, brought back a sense of community and saw fruit shops, tailors, groceries, fish and chip shops, cafes and clubs proliferate. By the early 21st century it was becoming fashionable again and in the last 10 years in particular it has evolved to be one of Melbourne’s most on-trend destinations. It retains its independent spirit and slight air of rebellion – no cookie-cutter chain stores here, please – and a proud, creative and supportive community whose people are passionate about their patch.

While the beauty of Gertrude Street is in discovering its gems for yourself – carve out plenty of time to explore – here are a few to kick off with.

Aesop Fitzroy

No two Aesop stores are the same, each subtly weaving itself into its neighbourhood, and Fitzroy’s pays homage to the history of its location in Melbourne’s first suburb. Odes to domestic rituals are found throughout and the basin, a signature of the locally born skincare brand, is rendered in concrete and inspired by the laundry troughs found in lean-to structures behind the area’s older houses.

Marion

Once you’ve established your local cafe, you’ll want to seek out your local wine bar. Look no further than Marion. Snag a seat at the window to watch the street life outside as you choose from a serious curation of drops sourced locally and from around the globe. Go for a glass and stay for a bottle and be sure to tuck into the seasonal menu of small plates and sharing dishes, from oysters to cheese to roast half chicken. Next door, and also in the Andrew McConnell stable, is fine diner Cutler & Co.

Archie’s All Day

Between its street-side seating where friends gather for brunch on weekends, suitably cool interior where creative freelancer types tap away on laptops, all-day menu and impeccable coffee by Proud Mary, Archie’s All Day is exactly the kind of cafe you’d expect to find in Melbourne. Make it your local, too, by ordering your caffeine fix of choice alongside a helping of smashed avo with Meredith Dairy goat’s cheese or huevos sucios (dirty eggs) complete with tater tots, jalapeño-spiked Monterey Jack, salsa and black beans.

APW Gallery

Pop into the Australian Print Workshop (APW) Gallery for a showcase of limited edition fine-art prints that represent the best of contemporary Australian printmaking, and for a window into the heart of Gertrude Street creativity. Celebrating 40 years in 2021, APW has witnessed the many evolutions of this cultural precinct in its dynamic role as a world-class printmaking workshop.

The Everleigh

This intimate cocktail bar inspired by the golden era of fine drinking is where you’ll want to cap off your day’s exploring on Gertrude Street. Hidden away, speakeasy-style (above Belle’s Hot Chicken, another go-to spot), this is – just quietly – not only one of the best bars in Melbourne, but in the world, as international awards attest. Slip into a booth in this sultry space and sip on a classic cocktail – an Old Fashioned or Moonlight, perhaps – crafted to exacting standards.

Morning Market

If there’s a silver lining to Melbourne’s long series of lockdowns, it’s the emergence of neighbourhood spots like Morning Market that began life as pop-ups and became permanent fixtures. Next door to Marion and Cutler & Co., Andrew McConnell’s one-stop shop for pantry staples and specialty grocery items also sells salads and sandwiches, cakes, pastries, pies and coffee; if it’s a sunny day, pick up provisions and walk five minutes to the top of Gertrude Street to Carlton Gardens for a picnic.

SMART, Alec Hatters

Catering to discerning gentlemen and progressive punks alike, Michael Albert will defy anyone to step inside his store and declare themselves ‘not a hat person’. Say the word and he’ll pluck a style from his eccentric collection to suit you: fedoras, boaters, bowlers, berets, trilbies – you name it. The dapper store owner and hatter is passionate about rehabilitating this ‘forgotten accessory’ and his charm, style and sharp eye will have you sold.

Builders Arms Hotel

The Builders Arms Hotel is a Fitzroy landmark and one of Melbourne’s oldest pubs, whose stones were first laid in 1853. It has seen it all since and remains at the heart of the community today under the aegis of (you guessed it) chef Andrew McConnell. Head here for a Sunday roast, Charcoal Chicken Tuesday, or perhaps for the best vegan cheeseburger you’ve ever eaten. Or simply sit outside with a Victorian pale ale and imagine all the lives that have walked by here over the years.

Discover our guide to the top Melbourne suburbs