A Weekender's Guide To Bowral and the Southern Highlands

Stay at a country estate, taste locally produced wine and whisky, peruse a whole heap of art and feast at a hatted restaurant — all in just one weekend.
Marissa Ciampi and Jasmine Crittenden
Published on April 16, 2023

The Southern Highlands may be just a 90-minute drive southwest of Sydney, but its string of villages, idyllic landscape and impressive producers will have you forgetting all about city life. Here, you can stay in a 19th-century estate, taste locally produced wine and whisky, peruse a whole heap of art and feast at a hatted restaurant — all in just one weekend.

And to help you get the most out of your trip to the Southern Highlands, we've put together a guide to the best places to eat, drink, play and stay. Grab your partner or some mates, base yourself in the lovely little town of Bowral for a few nights and start exploring.


Bendooley Estate via Destination NSW


Every weekend away should involve a good brunch, and Bowral offers just that in the form of The Press Shop. Part printing workshop and part cafe, the diner showcases Southern Highlands produce at its best with its farm-to-fork mentality. The cafe also offers one fine cuppa — though coffee-fiends may want to save their caffeine intake for Bowral's boutique roastery Rush.

At some point during the weekend, you'll need to make tracks to Bendooley Estate, which is on our list of ten awesome NSW cellar doors. But the 200-acre property doesn't just offer a cellar door — it's also home to a luxe restaurant, an alfresco cafe and an outpost of the much loved Berkelouw bookshop, with thousands of new, secondhand and rare titles. You can also expect stunning views across the vineyard and, of course, some fine regional wine.

Peppergreen Estate via Destination NSW

The whole region is home to over 60 vineyards and 17 cellar doors specialising in cool-climate wine varieties like pinot noir and riesling. You can use this handy Southern Highlands wine trail map to get you started. Be sure to include a stop at Peppergreen Estate, where you'll find wines on sale alongside extra virgin olive oil produced from the vineyards adjoining olive grove.

Then there's Artemis Wines, which has woodfired pizzas on every Saturday and Sunday — plus BYO vinyl nights, movie nights and yoga events occurring regularly, too. And you cannot miss trips to the award-winning Tertini cellar door and Tractorless Vineyard — at the latter, the biodynamic wines are made by letting sheep graze on the weeds in lieu of using machines and pesticides.

Wine not your thing? Whisky and gin fans should instead head to the Joadja Distillery, where free tours and tastings of its small-batch drops are on offer every weekend. Meanwhile, lovers of craft beer should stop by Eden Brewery in Mittagong — and pop across the road to Gumnut Patisserie for a pie to enjoy with your tasting paddle. And, if you have the cash to splash for dinner, be sure to reserve a table at Eschalot, which serves up fine dining from a quaint stone cottage in Berrima.


Dirty Janes via Destination NSW


The Southern Highland's boasts some pretty spectacular outdoor sights, including the well-known trio of waterfalls — namely Fitzroy, Belmore and Carrington — and an abundance of hiking trails. If you do plan on stopping by the Fitzroy Falls and have a few hours to spare, you'll be well-placed to complete the 1.5-hour West Rim walking track through lush rainforest. Alternatively, epic views of Bowral and Mittagong are on offer at Mount Gibraltar Reserve, or swap your bushwalk for a trip to The Southern Highlands Botanic Gardens in Bowral.

If you'd rather take things at a more leisurely pace, spend some time wandering through Bowral's many boutiques and specialty stores. You'll find a mix of eclectic and antique homewares at Barbara's Storehouse, Dirty Janes and The Bronte Tram, indoor plants at The Potting Shed and delicious handmade chocolates and marshmallows at Ms Peacock Confections.

Art aficionados can easily enjoy an art trail, with heaps of studios set in and around the Bowral town centre. Popular galleries include Bowral Art Gallery — which offers a regularly rotating lineup of exhibitions, painting workshops and events — and The Milk Factory, where the contemporary exhibitions are paired with a gallery shop selling resin jewellery and blown glass. Around the wider Southern Highlands region, you can also take sculpture classes, pick up some handmade ceramic homewares and even visit a puppet centre. Find more art options in the surrounding region over here.


Peppers Craigieburn


Bowral's small-town vibes make staying in boutique accommodation a must. Peppers Craigieburn offers just that — each of the rooms in this country hotel overlooks the expansive 36 hectare garden estate and private nine hole golf course. For something altogether more modern and glam, hit up Berida Hotel. Not only do you get spacious rooms with lavish furnishings and fittings, but you'll also have access to the hotel's own spa — an essential for anyone wanting to really spoil themselves on a weekend away in the Southern Highlands.

For those travelling on a bit of a budget, you can even rent a room at the local Bowral Hotel. This pub has a few motel-style rooms around the back that have been recently refurbished. Grab some pints and classic Aussie pub grub before taking the short walk to your room for a good night's sleep. It will help you have a proper local experience in the Southern Highlands.


Feeling inspired to book a truly unique getaway? Head to Concrete Playground Trips to explore a range of holidays curated by our editorial team. We've teamed up with all the best providers of flightsstays and experiences to bring you a series of unforgettable trips in destinations all over the world.

Top image: Destination NSW

Published on April 16, 2023 by Marissa Ciampi
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