Then, this most clearly delineated inner-Sydney suburb — a near-rectangle bounded by Regent Street, Broadway, City Road and Cleveland Street — was a blend of working-class and student accommodation, a smattering of light industry and, at its Central Railway end, absolutely dominated by the Kensington Brewery, whose initials provided the name for Tooths’ most popular beer.

The brewery is still a key ingredient of the suburb, but these days in the form of the Central Park redevelopment, which houses the completely revamped Old Clare Hotel, a myriad of accommodation options, a vast platter of restaurants and many artistic endeavours.

Many of the suburb’s old houses have emerged as trendy accommodation but many have been transformed into the edgiest of art spaces, which on their own form the basis for rewarding tourist visits.

One of the best ways in which to discover the inner workings of this fascinating new Sydney precinct is to take a walking tour with Culture Scouts, a knowledgeable, enthusiastic and passionate group of guides.

We were looked after admirably by Melinda Vassallo, who wears her artistic heart very much on her sleeve and provided an emotionally charged tour of not just Chippendale but also took us across Cleveland Street into Redfern’s once-notorious Block for a glimpse of how that was starting to change and gain artistic cred in its own right.

Eating wise, there’s plenty to choose from in the new-look Chippendale and I must admit to have only tried a few of them.

A few months ago I was blown away by the modern, cosmopolitan atmosphere, slick staff and great food at Kensington Street Social, which occupies some of the space in the Old Clare Hotel.

The kitchen takes centre stage, with many of the dining positions overlooking the workspace.

Current lunch-and-dinner menu entrées include Persian feta, served with smoked shiitake mushrooms, pickled pumpkin and nut crumble; and pasture-fed-beef tartare, served with beetroot jam, oyster emulsion, horseradish and wasabi leaf.

For main courses, select from a menu that includes dishes such as swordfish, served with parsley root cream, charred fennel and onion ash; and lamb rump, served with bacon, barlotti ragout, sprout chips and manchego (a milk cheese from Spain’s La Mancha region).

As at many good Sydney restaurants, the wine list includes a varied and eclectic offering by the glass, in this case with only a smattering of European wines holding fort against a strong Australian contingent.

I tried a few glasses, with my pick going to an elegant, smooth (no likeness to the name here), earthy Tommy Ruff 2014 Syrah Mourvedre from the Barossa Valley.

On my last visit, the Woman with Altitude and I thoroughly enjoyed breakfast, sitting on a bench outside a full-to-the-brim Brickfields, on the corner of Cleveland Street and Balfour Street, just outside the old Thurles Castle Hotel, formerly one of my favourite Chippendale watering holes and now a home for seniors at risk of homelessness. How appropriate.

It’s just so easy to see why this bakery/café is so popular with locals and visitors alike, and why they flock to it on weekends to chat, read the papers and gorge themselves on delights such as freshly brewed coffee, pastries, fresh bread and double-smoked-ham toasties with tomato chutney and cheddar.

It’s where we met our guide Melinda and it provided just the start and sustenance we needed for our adventure around Chippendale.

Lunch was at Ester, a relative newcomer to Sydney’s dining scene and one that has gained plenty of positive attention from the critics — including landing the award for best new restaurant by The Sydney Morning Herald Good Food Guide 2015.

The set-up, too, is appealing, and similar, in some ways to that at Kensington Street Social, with the kitchen very prominently on display to diners.

It did lead us back to the Old Clare Hotel for a cleansing ale and another look at a remarkable restoration job on this old inner-city watering hole, which was a revered drinking stop for workers at the Kensington Brewery and, after dark, a temple for Sydney’s indie-rock scene.

Here’s cheers to the whole experience of being reunited with a very different Chippendale to the one I knew as an up-and-coming sub-editor.

John Rozentals is a freelance writer whose passions are travel, food and wine. He lives at Molong in the Central West of NSW, from where he hosts Oz Baby Boomers, a lifestyle-resource for mature Australians, and Molong Online.