Getting behind the wheel is a pleasure when your journey covers landscapes as diverse as they are picturesque.

Driving Sydney to Dubbo? You’re in luck; it’s not so much a ‘Point A to Point B’ road trip as it is a 528-kilometre feast for the senses, all vibrant gold canola fields, misty mountain villages and more than a few wildflower-adored wineries.

There’s nothing to say you couldn’t make the journey in a little over five hours, but to do so would be to cheat yourself. Our advice? Break it up into a multi-day adventure and turn it into the ultimate regional New South Wales road trip for the ages. Here’s how:

Day one: Sydney to Blue Mountains

On paper, it’s only a 90-minute drive west of Sydney’s CBD, but in reality your car serves as the chariot which takes you into a world of charming villages teeming with antiques and secondhand bookstores, toasty cafes with crackling fires and more than a few scenic bush walks.

Hit the road early so you can make the most of the villages dotted on either wise of the Great Western Highway and pay close attention to Glenbrook, where excellent coffee can be found at Kickaboom or 2773 ; Lawson, where the pastries at Black Cockatoo Bakery are a must and Blackheath, home to the gargantuan Victory Theatre Antique Centre.

You’ll need your hiking shoes to tackle one of two, seven-kilometre walks that begin at Govetts Leap Lookout , or the spectacular Grand Canyon Track which winds around waterfalls and lush rainforest alive with all manner of native plants.

Rest and recovery can only take place at cherry blossom-lined Leura, where a vibrant mix of boutiques and eateries line ‘The Mall’. Make a beeline for Bygone Beautys Treasure Teaport Museum , stock up on handmade chocolates at Josophans , and – provided you have enough time – book in for a guided walk with a local at Mountains Tales .

Would a trip to the Blue Mountains be complete without a visit to the Three Sisters? Of course not, and happily, the new Katoomba Falls Reserve Night-Lit Walk is now open and there’s no better way to embrace the end of the day than by observing the iconic landmark lit up under an ink-black sky.

The place to eat: Blackheat’s Ateş , an Ottoman-inspired restaurant and wine bar with a focus on share plates created with the help of a 150-year-old ironbark-fuelled oven.

The place to stay: Lilianfels is a characterful accommodation that boasts heritage allure and is perfectly situated a short walk from some of the most iconic sites.

Day two: Blue Mountains to Bathurst

Start your day with a buffet-style breakfast in the light-filled The Orangery at Lilianfels.

Although a stop at Jenolan Caves (a little over an hour away) is always recommended when you’re in this part of the world,  it remains closed due to heavy 2024 flooding. The good news? Those who make the hour-long journey west to the adventure playground that is Oberon are handsomely rewarded with a wealth of State Forests, Lake Oberon and scenic cool climate gardens.

Got a thing for sapphires? Make the Oberon Visitor Centre your first port of call where you can pick up a fossicking kit and pick up maps for spots where you can spend a couple of quiet hours in shallow waterways fossicking for gems. Depending on the time of year your visit, you also have the option of signing up for a truffle tour with the likes of RedGround and Oberon Black .

No trip to Oberon is complete without a stroll around Mayfield Garden , one of the world’s largest privately owned cool climate gardens – best described as ‘a riot of colour demanded to be seen immediately’. It’s 65 hectare presence can be a lot to get through, but once you’ve had your fill of the gardens’ lake, box hedge maze, water garden and chapel – and assuming you’ve opted against having a picnic set up for you – take the 30-minute drive to Rockley, a perfectly preserved 19-century country village. Although home to a multitude of heritage buildings and pretty parklands, you’re here for a table at Matt Moran’s The Rockley Pub where the parmesan-crusted chicken schnitzel is on high rotation (and deservedly so).

Drive a further 30 minutes north and treat yourself to a night at Oakhill Estate , glasshouse cabins perched high above Bathurst where you can unwind in front of the outdoor firepit, enjoy a platter (or two) and sleep under the stars.

The place to eat: Cobblestone Lane has long been the place to be for those craving fine dining in an elegant heritage building.

The place to stay: Not into glass cabins? It’s hard to go past 232 at Boonderoo , an architecturally designed home which uses the thermal mass of the earth to achieve ultra low energy consumption. 

Day three: Bathurst to Dubbo

To start the day with a breakfast burger or pancakes topped with berries? No matter which way you swing, you won’t be able to deny you have the best table in the house at The Hub . Stretch the legs as you take a walk around Bathurst, the town where gold was first discovered in 1823 and where historic buildings such as the grand Bathurst Courthouse remain a sight to behold.

It would, of course, be criminal if you didn’t visit the Australian Fossil and Mineral Museum and Abercrombie House , a Scottish baronial mansion from the 1870s before taking a hot lap (or two) of the famous Mount Panorama Circuit .

Motor enthusiasts will consider a visit to the National Motor Racing Museum the ultimate diesel-covered cherry on top.

The bustling country town of Orange, a Mecca of award-winning restaurants, bountiful produce and cool climate wineries is only a leisurely 45-minute drive away, but making regular stops is all part of the experience.

Surrounded by some 60 vineyards, make a beeline for the likes of Philip Shaw , Ross Hill and Swinging Bridge and don’t miss grabbing a table at Swinging Bridge which offers an in-depth tasting of their wines paired with a five-course degustation. Road trippers will need to remember to use the spitoon, however.

Orange is home to a wealth of quirky boutiques – many of them located on Sale, Summer and Byng Streets. Once you’ve browsed the racks and stands of The White Place , JUMBLED and Mary & Tex Curious Emporium , and embraced Orange’s vibrant cafe culture with a pit-stop at Byng Street Local Store or Good Eddy , lock in a bush tucker tour slot with Indigenous Cultural Adventures , run by the charismatic Gerald Power.

The place to eat: Don’t miss a meal at The Union Bank where a whole barramundi is served with prawns and toum in an elegant setting.

The place to stay: It’s hard not to be dazzled by the romantic glamping options at Nashville Lane , where you can enjoy quality produce (and fine wine, of course) by the fire.

Leave Orange early for your 90-minute drive to Dubbo. As you can imagine, there’s a lot to discover!