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A Weekender's Guide To Bowral and the Southern Highlands

Stay at 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.
By Marissa Ciampi and Jasmine Crittenden
May 29, 2020
By Marissa Ciampi and Jasmine Crittenden
May 29, 2020

in partnership with

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.

The region has always been worthy of a visit, but now it's more important than ever. The area was recently devastated by bushfires, and many local businesses have suffered greatly. So, we've put together a guide of where to eat, drink, play and stay during a weekend getaway to the area. Grab your partner or some mates, base yourself in the lovely little town of Bowral for a few nights and start exploring.

From pristine beaches and bountiful wine regions to alpine hideaways and bustling country towns, Australia has a wealth of places to explore at any time of year. We've partnered with Tourism Australia to help you plan your road trips, weekend detours and summer getaways so that when you're ready to hit the road you can Holiday Here This Year.

While regional holidays within NSW will be allowed from June 1, some of the places mentioned below may still be closed due to COVID-19 restrictions. Please check websites before making any plans.


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. And now is especially the time to support local farmers. 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 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 Chocolatier.

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.


Bendooley Estate via Destination NSW


Bowral's small-town vibes make staying in boutique accommodation a must. Links House Hotel offers just that — expect charming 1920s-style rooms surrounded by rose gardens and courtyards. Or book into The Sebel Bowral Heritage Park, which provides a bit more space with one- or two-bedroom contained apartments. And, if you're looking to stay around the greater Southern Highlands region, it's hard to go past Bendooley Estate, where its spacious cottages allow you to thoroughly enjoy the estate's many offerings.

For those travelling in a large group, you can even rent an entire former coach house on the grounds of The Rift Estate, a 19th-century Italianate mansion. This house sleeps up to 13 people, and is situated on Bowral's outskirts — but within walking distance of the town.


Whether you're planning to travel for a couple of nights or a couple of weeks, Holiday Here This Year and you'll be supporting Australian businesses while you explore the best of our country's diverse landscapes and attractions.

Top image: Destination NSW

FYI, this story includes some affiliate links. These don't influence any of our recommendations or content, but they may make us a small commission. For more info, see Concrete Playground's editorial policy.

Published on May 29, 2020 by Marissa Ciampi
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