This season, “Go to jail. Go directly to jail. Do not pass go. Do collect a friend to go along with you.”

Coburg is now a delicious day-trip destination (one that you barely need to leave town to enjoy). At the time that the infamous Her Majesty’s Pentridge Prison was shut down in the late 90s it was nearly 150 years old. In its wake; drinking, dining and a number of immersive experiences.

First stop; a long, languid lunch at North & Common. Though glimpses of what was remain, you’d never in a million years guess that this inviting space was once a prison mess hall. Designed by CHADA, the space is swathed in a soft, nature-inspired colour palate including subtle terracotta tiles and lofty ceilings; which somehow pulls off “cosy” and “airy” simultaneously.

If it’s a rainy day, situate yourself near the large open windows to watch as grey skies fall with a peanut butter-infused bourbon Old Fashioned in hand while you peruse the menu. If it’s balmy, take your vermouth on the rocks out to “The Yard”; the hatted restaurant’s version of an al fresco terrace. Here, you can perch yourself on a Parisian chair and pick over the prettiest pastel pink and green cured kingfish dish.

Also try their plump knot of burrata plonked in a field of earthy heirloom tomato bathed in “this is what tomatoes from my pop’s garden used to taste like” oil. Or for something more substantial, go for generous slices of perfectly pink lamb rump dolloped with creamy labne – it’s your weekend roast, only elevated. Do remember to save some sourdough to soak up whatever’s left on your plate (lest you be tempted to lick it clean in public).

That’s the lunch order sorted. Would you like a side of history with that? On Saturdays, North and Common is currently serving up two courses alongside a tour of the heritage-listed Pentridge Prison (R.S.V.P. here – Thursday evenings are also an option). After lunch, they’ll escort you to the old Warder’s quarters before a guide takes you wandering through what remains of the prison grounds and through the notorious H Division.

The stark, Classical architecture of the prison, constructed in locally-sourced bluestone, reflects the often bleak stories that were written behind these walls. It’s dark and fascinating. And probably haunted. But there are light-hearted moments. Did you know there was once a splash pool for prisoners’ leisure here? And local schoolboys would climb on in to retrieve stray cricket balls? Aside from numerous yet short-lived escapes, the inmates also put on jaunty theatre productions.

Then again, there’s a reason the H Division (or “Hell” Division) is an essentially adults-only tour. Once you enter this maximum security wing, you’ll go on a choose-you-own-adventure-style audio-visual exploration of the lived experiences of both the prison’s “reluctant guests” and guards.

After such eye-opening education, it’s understandable if you’re in want of a stiff drink. Happily, Olivine is here to help. This sophisticated wine bar makes full use of its unconventional location. Sitting here with a glass of Blanc de Blancs, it’s funny to ponder how much an ex-prison shares in common with a traditional wine cellar. Aside from a sprawling wine list, Olivine also makes a mean cocktail. Sip a luscious, laid-back Honey Man (bourbon, sweet vermouth, honey, orange bitters). Best enjoyed inside one of the former cells now converted with plush, rich furnishings into semi-private imbibing nooks.

It’s easy to make a weekend escape of it. Aside from North and Common, Olivine and Pentridge history, there’s also Brewdog Brewery, The Boot Factory (actually a café) and a cinema on site. Overnight, staycation at The Interlude. This boutique hotel is designed as an urban retreat with an underground bathing pool and “reflection garden” complete with campfire. The luxury suites, dressed with artisan interiors and goods, are even fashioned from interlocked prison cells – though you won’t feel in any way trapped. Just captivated.