The Southern Highlands is the beautiful cool climate wine region south of Western Sydney and should be at the top of your list for a weekend getaway. There are a multitude of great wineries locally but for something different we wanted to explore not only great wineries but also the small bars, and some of the most charming boutique accommodation.
The Southern Highlands is a truly beautiful area and is the traditional land of the Gundungurra and Tharawal people. Ngurra (Country) means everything. It is physical, cultural, and spiritual and you will certainly get a sense of this as you explore for yourself.
With so much to explore the best way to get around is by car. With new EV charging locations scattered across the Southern Highlands you can do this effortlessly and in style. We suggest you spend the day exploring some of the wineries and their cellar doors and then venture to some of the small bars in the late afternoon and into the evening. Finish your adventure at the Mittagong Hotel which just won some interior design awards for its stunning accommodation and is the new MUST-VISIT place to stay in the Highlands.
Start your day here, on Joadja Road. You’ll find a very special small-batch winery and cellar door – Joadja Estate. Opened in 1983, Joadja Estate is proudly the oldest vineyard and winery in the Southern Highlands, offering a rustic family friendly experience surrounded by the hills and greenery of this stunning wine region.
You will love the relaxed atmosphere of this boutique winery where time almost stands still. Visit for a wine tasting either inside the cellar door or outside in the beautiful garden. It’s the perfect place to slow down, relax, and learn about the wine region and variety of wines made at this local’s favourite winery. From Sauvignon Blanc, Summer Rose and Cabernet Merlot to their ever-popular boysenberry liqueur, Joadja Estate’s years of experience can be tasted and enjoyed. Don’t forget to order a delicious charcuterie board on the Joadja Estate website when you book your tasting, so you are guaranteed to make the most of your time here.
The Estate is also the place to be on summer Saturdays and on long weekends, with their free Music in the Vines live music series. On concert day, the winery also offers a selection of piping hot pizzas from the pizza oven to complement your favourite bottle of wine. The combination of talented local musicians with good wine, food, and stunning vineyard views, is perfect for memory making.
Joadja Estate is a must-visit winery and cellar door doing it right and always making you feel like family. With plenty of events, enviable wine selection and unforgettable Southern Highlands sunsets, it’s a destination to return to time and time again.
A little further west along Joadja Road is the Joadja Distillery which is located in an abandoned kerosene shale mining village from the 1800s. This is a great little country drive where you can sample some amazing gins and whiskeys. Bookings are not essential but are advised.
In Mittagong, you’ll find the sunny winery Artemis Wines. They have a fantastic casual atmosphere, woodfire pizza, and live music. A great day in the sunshine but with so much to see, stop in for a tasting and be sure to try their mead.
Heading south and already a well-known destination for food and wine, Bendooley Estate is popular for day visitors and for weddings and events. The estate is expanding its existing wine production and has, just out the back of the main food and book barn, one of the most elegant cellar doors. This is a great place for not only a wine tasting but you can just drop in for a single glass of sparkling, white or red wine. Locals know this and enjoy the cellar door for a casual glass overlooking the vineyards.
Our day trip takes you on a loop through the countryside and the next stop is Cherry Tree Hill, just off the Hume Highway in Sutton Forest. To get there you will pass through charming Berrima so if you need a coffee or something to eat it’s a great stop along the way. Cherry Tree Hill also offer a lunch menu, but make sure you book in advance. You’ll find light meals, tasting boards and delicious gourmet pies. The cellar door is full of charm with stunning views down the hill and across the vineyards.
Further south and heading towards Bundanoon you are in the heart of wine country where you’ll find Eling Forest Winery, Southern Highlands Winery, St Maur, and heading into the village of Exeter you will find Dawning Day Farms. This is a great stop to try a flight of local cool climate wines – make sure to try their personal favourite Gamay. As their name suggests, you’ll also find a variety of produce including their range of homemade pickles, hot sauce, and Limoncello.
Stop in for a local produce platter, tasting, and chat. A day well spent!
Next on the list is Osborn House in Bundanoon. A great place to stay overnight and one of three options that also offer a destination in and of itself. This Boutique Hotel has a great bar and offers an Argentinian BBQ feast that you must see to believe. Great local wines on offer and sumptuous lounge areas indoors with ridiculously beautiful views over the Moreton National Park.
In the heart of Moss Vale is Highlands Taphouse, a local institution with great energy in the late afternoon and far into the evening. Proudly displaying local beers, wines and incredible dishes, Highlands Taphouse is a celebration of the high quality produced in the Southern Highlands.
We love the updated interior of the Taphouse which feels like a classic living room. With freshly painted walls, country-style furniture, and quirky paintings, the Highlands Taphouse really has its own character which is loved by locals and visitors alike.
Order a beverage from their list of locally produced wines and beers and enjoy it in their street front seating watching the passers-by. There’s nothing like a slow twilight drink here!
And when it comes to food, they’ve nailed it too. Highlands Taphouse has an excellent à la carte menu using ingredients sourced locally. The excellent ‘From the Grill’ menu offers the best cuts of meat sourced locally in Exeter. From sophisticated starters, mains, and dessert, you’ll want to dine your way into the night. And of course, with exceptional service, we love that you’re made to feel right at home here.
Relax, get comfortable, and enjoy the atmosphere of beautiful Moss Vale at one of the Southern Highland’s most charming venues. This is a must-visit destination loved by locals.
The Berida Hotel in Bowral has two bars on offer and the all-important EV charging location. The aptly named bar, The Gin Trading Co, has one of the biggest collections of gins with signature cocktails and bar menu within their contemporary European cuisine restaurant Bistro Sociale. If you’re feeling like something stronger, they also have the Aspinalls Whiskey Bar & Lounge which is equally as popular in an elegant and timeless setting.
Making your way back towards Mittagong, it’s worth stopping by Eden Brewery at the base of Mount Gibraltar (‘The Gib’ to locals). This artisan brewery is open day and night and is a great place to try an ever-changing array of artisan beers. The food truck out front is popular with locals and on a clear day or night you will see a regular crowd gathering.
Located on the main road just near the main intersection you’ll see a rich red door for Hendriks Bar & Grill This is a relaxed vibe with regular live music, great food and an extensive wine featuring both local and French wines of great standing. Grab a cheese board as you settle in for the night.
Mittagong Hotel is a beautiful and historic hotel with a paddock-to-plate ethos and a very rich history. The building dates back to 1890 when it was built as a hotel on Mittagong’s main street. It was popular in the early 1900s among all townsfolk, bicycle clubs, and billiards players. Mittagong Hotel, as we know it today, was reopened in 2023 and has reinvented the idea of a country pub with sophisticated styling that not only looks sleek but preserves the historical features of the hotel.
Sit down in their cosy Front Bar for a cocktail, beer, or wine at any time of the day. In true local pub style, Mittagong Hotel serves a range of local beverages – perhaps from places you visited earlier in the day. You’ll find Highlander Beer & Brewing Co, Cherry Tree Hill Wines, Bendooley Estate, and so many others.
For a meal, the Mittagong Hotel is again exceptional. All their meals are sourced with the best local and fresh ingredients, giving you an authentic Southern Highlands experience. Enjoy familiar pub classics each with a contemporary twist by head chef Luke Kerlin. With a welcoming atmosphere, you’ll want to stay and enjoy the place for hours.
You might even want to stay a night here – after all, Mittagong is simply beautiful. With fourteen modernised rooms, you can enjoy a weekend of country charm here. Their rooms feel so luxurious, with fresh new carpet, a warm colour scheme and classic finishes, it will be your haven for the weekend.
The reality is all the vineyards in the Southern Highlands really are exceptional - each cellar door offers something unique. Even the local pubs will have a great selection of local wines and gins. And it's truly the same with the bars, which each have their own flare and character worth experiencing.
We love that whenever we visit the Southern Highlands, there's something new to stumble upon and discover.