Tantalisingly close to Sydney, yet a world apart, Kangaroo Valley lends its name to both a pretty village and one of Australia’s most beautiful river gorges, carving its way through the verdant and vine-covered slopes of the Southern Highlands in New South Wales.
The picturesque scenery is as exciting as the wine produced here. Lush and dramatic with waterfalls like Fitzroy, Belmore and Gerringong pouring over sheer cliffs; sublime swimming spots such as historic Hampden Bridge (below); and panoramic lookouts over unspoilt leafy landscapes to the glittering ocean.
The rolling countryside and fertile farmland would seem very British if it weren’t for gum trees, kookaburra cackles and (as the name suggests) wild kangaroos, bounding across open pastures.

Hampden Bridge, Kangaroo Valley. Credit: Dee Kramer Photography
On the wine trail
Encounters with the marsupials soon became commonplace on our three-day road trip of the Southern Highlands Wine Trail during mellow April, with trees turning autumnal and harvests (including grapes) underway.
Our aim was to discover this area’s increasingly renowned cool climate wines, made from varieties including Pinot Gris, Chardonnay, Pinot Noir and Shiraz. With some sites planted at over 700m, with snow possible in winter, grapes ripen slowly with enhanced flavour and intensity.
For those in the know, Southern Highlands vineyards are closer to Sydney and less frequented than the more famous Hunter Valley further north.

Kangaroos in Kangaroo Valley. Credit: Martin Berry / Alamy
Getting started
Bustling Bowral with its homeware shops, bistros and Dirty Janes antiques emporium, is an ideal base as it can be reached by rail. But with quiet roads and wineries often out in the sticks, it’s also fun to hire a car (although tasting is obviously limited unless you have a teetotal driver).
For those without wheels, a choice of guided wine adventures are available, like Tasting Tours Co, sister to the town’s central Bowral Cellar Door on the quirkily named Bong Bong Street, where outdoor tastings and local artisan snacks can be enjoyed.

On the wine trail in Kangaroo Valley. Credit: Destination NSW
Around Berrima
Be sure to stop at Bendooley Estate, Berrima, not least because this winery offers luxury lodgings. On a sunny afternoon, we happily sat at an al fresco table for our bargain AU$15 (£7) person wine tasting, served with appetising charcuterie and cheese platters.
After lunch, we browsed the shelves of Berkelouw Book Barn, doubling as an atmospheric and spacious alternative restaurant venue as popular for celebrations as for coffee, cakes and meals. Arty sculptures among the vines include an Insta-worthy giant corkscrew.
It’s a joy to explore Berrima, a preciously preserved 19th-century village with indy shops, an aroma-filled bakehouse and street-side cafés. PepperGreen Estate, in an ivy-covered heritage building with a vintage truck at the cellar door, produces olive oil and Olive Leaf Gin as well as fine wines. Try the mouthwatering menu of in-house experiences from masterclasses to wining and dining.

Autumn at Centennial Vineyards. Credit: David Wall / Alamy
Concerts and festivals
We were sorry to have just missed Fatboy Slim perform at nearby Centennial Vineyards, where Tom Jones and Rod Stewart headlined in previous years. The first and only five-star Halliday-recommended winery in the Southern Highlands is thus as famous for its legendary concerts and high teas as it is for its award-winning vintages.
Harvest here lasts from late March to early May (autumn in NSW). But other good times to visit include the Winter Wine Festival in June. Bowral’s Midwinter Festival happens in late July; while the annual Tulip Time Flower Festival runs from September to October and Bong Bong Picnic Race Day is in November.
For more information check out visitnsw.com

Canoes, Cool Climate Wines and Canapés Experience. Credit: Destination NSW
My perfect day in Kangaroo Valley
Morning
Kickstart the day with a PepperGreen Estate Sparkling Breakfast Experience in the tasting room at Berrima, quaffing Brut 2018, juice and coffee whilst scoffing caramelised French toast, honeycomb butter, toasted pistachios and vanilla extra virgin olive oil ice cream (from AU$100/£47). Stay for a tasting or pop into the region’s ‘oldest’ winery Joadja, converted from a dairy farm in 1983. Drive through pristine rainforest to Beehive Point to encounter native wildlife including curious wallaroos and water dragons wandering the banks.
Lunch & afternoon
Noon is departure time for the glorious guided Canoes, Cool Climate Wines and Canapés experience in double and reassuringly unsinkable canoe rigs seating four (AU$225/£107). You can easily spend two hours on Kangaroo River, paddling and popping open a surprise sparkling Shiraz from Centennial Vineyards or Two Figs Brut Cuvée NV to sip with tasty sandwiches and quiche in the company of kingfishers and koalas. Then it’s a 20-minute drive to quirky Kangaroo Valley village for refreshment in the historic Friendly Inn’s legendary beer garden before pottering around antique stores, bottle shops and the Pioneer Village Museum.
Evening
Check into Paperbark Camp in Jervis Bay, and say ‘G’day’ to wild kangaroos. Relish an apéritif by the Sundowner Deck’s firepit and spotting shy possums before an imaginative paddock-to-plate dinner paired with regional wines at treetop Gunyah dining room. Be spellbound by the Milky Way, under guidance of Jervis Bay Stargazing on a moonlit beach or while soaking in the private outdoor bathtub of your luxury tent.

Paperbark Camp in Kangaroo Valley. Credit: Paperbark Camp
Your Kangaroo Valley address book
Where to stay

Wilde’s Boutique Hotel. Credit: Grainger Films
Enjoy picturesque lakeside, valley and vineyard views from luxurious accommodation in studios or two- and three-bedroom cottages.
Spacious studios and suites with private courtyard or balcony, a restaurant, bar, pool and attractive outdoor terrace at this friendly Kangaroo Valley hostelry.
Inspired by African safaris, this upmarket, eco-friendly glamping site near Jervis Bay has en-suite, all-mod-con tents with baths under the stars, and candlelit, treetop dining.

Deluxe tent at Paperbark Camp. Credit: Paperbark Camp
Where to eat
Located at Bendooley Estate’s Cellar Door, this memorable dining experience combines exquisite flavours with a welcoming ambiance enhanced by crackling fireplaces and a home-grown wine list.
Hearty Aussie pub grub in one of the region’s oldest (1891) and most characterful bars. There’s also a bottle shop and perhaps the world’s best beer garden offering panoramic sunset views over Kangaroo Valley.
Aboriginal for ‘meeting place’, treetop dining focuses on seasonality and sustainability elevating bush tucker to new heights with a curated selection of regional wines.

The Friendly Inn, Kangaroo Valley. Credit: Robin Weaver / Alamy
How to get there
The nearest international airport is Sydney, from where you can drive in around 90 minutes to Bowral via the M5 or catch a direct train (pre-book in advance) from Central Station, taking 1.5 hours. Slower trains via Campbelltown are also available.
For a more leisurely road trip, visit the Blue Mountains en route, for the unique Buunyal Tour and Scenic World attractions.Then follow the M31 to Bowral. It’s just another 30-minute scenic drive south to Kangaroo Valley, from where you can return to Sydney via Jervis Bay with its white sand beaches and dolphin cruises along the dramatic coastal road.