Look down as you walk past the Glasshouse arts centre in Port Macquarie and you’ll notice dark brick-shaped lines across the footpath. They were put here to mark the location of cottages that once stood on this spot, with some of the foundations protected and still visible in a small museum in the Glasshouse’s basement. The cottages belonged to the convict overseers of the harsh and isolated penal colony founded here in 1821, which will be commemorated this year as the official bicentennial of Port Macquarie.

Heritage consultant Mitch McKay leads tours through the city to uncover this convict history, bringing the stories to life through his research and the original buildings that remain.

Mitch McKay leads one of his heritage tours through the Port Macquarie Historic Cemetery.
Mitch McKay leads one of his heritage tours through the Port Macquarie Historic Cemetery.

“There are things that you’ll see in Port Macquarie that you won’t see anywhere else on the eastern seaboard of Australia,” Mitch tells me. “It’s always advertised as sun, sand, surf, but the thing that sets us apart from all these other sun, sand, surf destinations is our heritage.”

Mitch shows me some of this at St Thomas’ Anglican Church, opened in 1828, and one of only two in Australia that has pews surrounded by wooden boxes, protecting the free families from the prisoners sitting on the floor. And then we take a stroll through the cemetery where more than a thousand people were buried but just 88 grave markers remain, each with a fascinating – and often quite harrowing – tale about life in a penal settlement designed for the most irredeemable of prisoners.

The boxed pews of St Thomas' Anglican Church, opened in 1828.
The boxed pews of St Thomas’ Anglican Church, opened in 1828.

“This wasn’t a holiday,” Mitch quips as he finishes one of his stories.

Oh, how times have changed. Port Macquarie is now, of course, everything a holiday should be! The convicts had to come by ship (there was no road back then) but we have the luxury of jetting in, with direct flights from Canberra, Sydney, and Brisbane. I take the modern mobility to the extreme and also join Affinity Aviation for a sightseeing helicopter ride, swooping over the glittering coastline with views across to the mountains and rivers. Affinity offers a range of affordable packages, including trips to waterfalls or regional restaurants. In my case, I feel like a celebrity when the helicopter drops me off at Cassegrain Wines and waits until the end of my tasting!

Part of the nine-kilometre coast walk past some of Port Macquarie's beaches.
Part of the nine-kilometre coast walk past some of Port Macquarie’s beaches.

Cassegrain is one of a few wineries in Port Macquarie, a region where you might not expect to find vineyards but that actually offers a good range of winemakers. Cassegrain draws on the French heritage of the family but sources its grapes from about half a dozen areas around New South Wales, allowing it to choose varieties from appropriate regions. But to taste the grapes grown onsite, try the semillon and the chambourcin (which also comes as a sparkling, made with the traditional method of Champagne).

“Because a lot of people come here and they say it’s not a grape-growing region that they know, even though it’s one of Australia’s first, it does take that conversation to convince people and get them to know there are premium wines here,” the winery’s Phil Cassegrain explains.

Phil Cassegrain at his family's winery, Cassegrain, which sources grapes from across NSW.
Phil Cassegrain at his family’s winery, Cassegrain, which sources grapes from across NSW.

I don’t need much convincing after the free tasting to head to the winery’s new restaurant, twotriplefour, where the menu reflects the region’s best local produce, a farm-to-table approach that changes with the seasons. The selection of grazing plates – including my favourite, beetroot cured ocean trout gravlax – are just the right size for a summer lunch paired with a glass of wine.

Cassegrain wines paired with a tasting plate from the onsite restaurant, twotriplefour.
Cassegrain wines paired with a tasting plate from the onsite restaurant, twotriplefour.

The twotriplefour restaurant is the inland sister to the acclaimed Bills Fishhouse + Bar near the waterfront. They are part of the dining renaissance of Port Macquarie that is helping the city shrug off the perception that it’s just about a barbecue at the holiday park (although that’s certainly still popular). Many visitors now expect top dining options, and they don’t get much better than one-hatted The Stunned Mullet.

There was an evolution for The Stunned Mullet, which opened in 2005, to become the fine-dining proposition you find today, and it still has enough of a casual atmosphere to feel relaxing on a coastal holiday. I highly recommend the signature dish, the Glacier 51 Toothfish, caught 4000 kilometres from Australia deep in the sub-Antarctic. The wine list is also impressively extensive, sourced from across the world.

Although it’s busy in Port (as I’ve started calling it after just a day here), it never feels hectic or pretentious. But it’s not hard to escape any crowds with a short drive to one of the long empty beaches or smaller communities nearby. About 30 kilometres south is Dunbogan, where the village of 1000 people is done being bogan (sorry, I couldn’t resist). The historic 1937 boatshed, the community’s focal point, has been turned into a wonderful cafe and recreation hub, where you can rent boats or kayaks, feed the fish, or just relax on the deck.

The Dunbogan Boatshed has been an important part of the local community for generations.

Soon, Dunbogan Boatshed owner Damien Lay will also be launching boutique river cruises with options for a platter lunch, Devonshire tea, or even oysters picked up from a local farm en route. And he also has plans to convert an original trawler into a chic bar on the water, creating a destination out of a village that doesn’t even have a sign at the turnoff from the main road.

Exploring the waters just south of Port Macquarie on a cruise from the Dunbogan Boatshed.
Exploring the waters just south of Port Macquarie on a cruise from the Dunbogan Boatshed.

“When people do come out to Dunbogan, it’s interesting to see people’s reactions,” Damien says. “It does feel like they’ve actually discovered something brand new that they’ve never heard of.”

There’s quite a bit to discover (old and new) around Port Macquarie, including the Koala Hospital (which gained notoriety after rescuing animals following last summer’s fires), the nine-kilometre coast walk to the Sea Acres Rainforest Centre, and the colourful paintings on the rocks of the breakwall. The city has come a long way since that convict colony 200 years ago, and it’s proven it’s not a prisoner to its past.

Take me there

What to do:

Where to eat:

  • Perfect for lunch after a wine tasting, twotriplefour at Cassegrain has a paddock-to-plate approach.
  • For a popular seafood restaurant in the centre of town, there’s Bills Fishhouse + Bar.
  • Probably the best dining experience in Port, don’t miss The Stunned Mullet for something special.

Where to stay:

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