Southern Highlands: How to eat, stay, love in picturesque heaven

When the locals developed the Pie Trail with about 30 highlands pie outlets, they probably didn’t expect anyone to try to eat at all of them… but it’s a tempting notion seeing as the region’s bakers are constantly competing with each other to create new and interesting varieties. There’s the lamb and rosemary from Gumnut, a chicken with leek and camembert from the Robertson Pie Shop, or the Ned Kelly (a breakfast pie with beef, egg, and bacon) at Heatherbrae’s.

It’s been a while since I’ve been to Bowral. The beef pies taste vaguely how I remember but one of the town’s other icons – the Bradman Museum – has changed a lot. In fact, it’s now evolved to become quite a pilgrimage site for fans and includes the International Cricket Hall of Fame, which tells stories of the sport’s important eras and has an impressive collection of memorabilia.

“When Bradman was first invited to be part of this museum and was asked to give his name to the museum, one of the things he said was that he didn’t want it to be just about him,” museum curator Andrew Summerell says. “He wanted it to be about the history of cricket as well, and about world cricket.”

The museum is always changing and a new gallery about women’s cricket will be coming soon. But it seems the Southern Highlands overall has also been changing in recent years. The region has long been a country escape for Sydneysiders and traditionally many of the houses were just for weekend visits. But now it’s quite common for someone’s primary residence to be here (perhaps with a weekender in Sydney). And this shift has only strengthened the local community.

I chat about this with the owners of the Grand Bistro in Bowral, Justine and Damien Monley, who used to run a cafe in the affluent Sydney suburb of Woollahra. They brought some of their favourite dishes with them, like their famous 7-hour lamb sandwich, but customers are also interested in produce from the region.

“They want to know, whatever they’re eating, if it’s local. They really embrace the local stuff,” Damien tells me.

“And we’ve got some wonderful producers like Redleaf Farm – she does the most amazing suckling pig, so we might run that as a special every now and again.”

The ‘she’ that Damien is referring to is Katrina Sparke who, with her husband Sam, runs a farm with pigs, cows, sheep… and a whole menagerie actually, including peacocks and an adorable miniature donkey called Hector (who I can’t resist patting when I visit).

You can arrange farm tours and other experiences across the sprawling property that has a waterfall and swimming hole. But for something really special, stay in one of the two train carriages that have been converted into extraordinary self-contained accommodations.

The fertile lands in the Southern Highlands lend themselves not just to farming, but to vineyards, and a number of local wineries have made a name for themselves, including Centennial Vineyards, Artemis Wines, and Cherry Tree Hill. But nothing quite prepares me for Bendooley Estate, which feels like a destination in itself. With a bookshop at its core, the shelves merge into a cafe, a stylish restaurant, and a bar for wine tastings. I settle in to try quite a few drops and am particularly impressed by the oaky Pinot Noir, a varietal that this cool-climate region is well known for.

Bendooley Estate is on the way to historic Berrima, established in 1831 with plans for it to become a major town. That never quite happened but, along with the well-preserved Georgian main street, there’s the sandstone courthouse and gaol. Although the gaol is restricted because it’s in use again, you can visit the courthouse to learn about the town’s history. One of Berrima’s best heritage buildings now houses the excellent Eschalot restaurant where Matthew Roberts and Cass Wallace serve interesting modern dishes (I would recommend the tasting menu, which includes pork belly and crispy fried chicken).

Harper’s Mansion on the edge of Berrima is an interesting National Trust property but, of those in the Southern Highlands, the most impressive is clearly Retford Park. Built in 1887 by Samuel Hordern, it was bought in 1964 by James Fairfax who transformed it into a sumptuous country residence. A driveway curves up through the large landscaped gardens to the Italianate-style four-bedroom residence, which is still fully furnished. James Fairfax bequeathed it all to the National Trust before he passed away in 2017 so it could be opened to the public.

“We like to make it feel like he’s just stepped out, he’s just left the place,” Curator Ann Frederick explains as she shows me around. “So these are some of his furniture and his antiques, and a lot of his artwork is still here.”

It’s easy in the Southern Highlands to get caught up in the antiques and the heritage – or, if that’s not quite your thing, the food and the wine. But it’s important to remember that this is also a naturally spectacular region. The orange glow as the sun sets over the rolling green hills, for example, or you’ll even find rainforest at Macquarie Pass National Park.

My favourite spot, though, is Fitzroy Falls in Morton National Park. The dramatic 80-metre waterfall is the centrepiece of the site but there are easy walking tracks along the cliffs in either direction that offer different perspectives and lead to smaller cascades. The views here remind me of the escarpments of the Blue Mountains and are, in many ways, just as dramatic. Rambling between the lookouts, I actually manage to build up a bit of an appetite. Luckily, I know just the thing to grab for a quick bite and my Pie Trail map shows me there’s a bakery nearby (I did warn you earlier I hadn’t eaten my last one!).