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The Wollondilly Shire is in the South-Western fringe of Greater Western Sydney and is one of the largest but least populated areas within Western Sydney. Home to the Gundungurra, Dharawal and Dharug peoples, modern-day Wollondilly is rich with history, proud communities, and expansive landscapes. WEST takes you on a scenic drive along the Old Hume Highway and Remembrance Drive. Be ready for a day full of delight, pleasure, and welcome discovery.

Train crossing old arched bridge


The journey WEST is taking is a favourite of motorcyclists with a beautiful, easy, and scenic drive past, through, and over several old bridges. Perfectly proportioned and oozing in character this is a great day out in the affectionately named The Dilly.

The road we are taking today is a part of Tourist Drive 12, which loosely follows the Main Southern Railway Line and is known by some as the Seven Bridges Drive. It begins in Picton and heads south through the Wollondilly Shire to Tahmoor, Bargo, and Yanderra.

Starting your day in Picton, you will discover a town full of history that is well preserved. Formerly on the Great South Road of Cobb & Co fame and Old Hume Highway, the town was originally named Stonequarry and then in 1845 renamed Picton. Here the town boasts great cafes and eateries that are much loved by locals. Coffee is always a great start to the day and there is a great collection of cafes including Picton Social, Moses Barnes, Leaf & Bean, The Ark, and La Crema, and the locals love them all.

An Historic Picton Walking Tour is a great way to explore, and you can get up close and personal with many grand old buildings, the heritage railway station, the incredible Picton Railway Viaduct (WEST have visited this before), the locally famous Mushroom Tunnel and the characterful George IV Inn nestled on the edge of Stonequarry Creek.

Bursting with character and history “The George” is the meeting place for locals, travellers, and motoring enthusiasts alike. This inn is home to a collection of buildings, including the oldest in Picton and delivers a genuine country pub experience. Once a Cobb & Co stop on the Great South Road between Sydney & Canberra, it’s a place full of history.

Pub classics sit side by side on the menu with some great contemporary and tasty food offerings. We also highly recommend trying a local at the local; Cedar Creek Cider. Produced right here in the Dilly at Cedar Creek Orchard, this apple cider is a perfectly refreshing beverage loved across Western Sydney.

Cedar Creek Orchard has been growing apples and persimmons for over 50 years. Visit the shed to buy fruit, juices and ciders – or check their website to make a Pick Your Own fruit session if in season.

The first arched stone bridge, typical of this drive, is right at the end of Picton’s centre. You can’t miss it, as it goes over the road heading south. As you pass through the outskirts of Picton, you’ll see many old buildings and country scenery towards Tahmoor.

Tahmoor is a thriving hub of growth and activity in the shire and home to many local stores, shops, and of course cafes. Stop on the outskirts just south of the village centre to take a view from one bridge to another. These arch elegantly right over the Bargo River and is a great photo opportunity too.

We continued to Bargo, another village we have visited before. Home to many great hikes and attractions like the Australian Wildlife Sanctuary. If accommodation is desired look no further than the beautiful five-star Kalinya Estate. A popular destination in its own right – book ahead and get in early!

Along the way as you follow the railway line, you will spot another arched bridge, this time brick- a more classic country charm and part of the character of this area. As we head towards Yanderra we will take a quick detour, this time across the Hume Highway (yes, another cute little bridge), and over to the Nepean and Avon Dams.

The vintage character and nostalgia of the parkland spaces around the dams themselves are once again very popular with day trippers. The bygone age of the picnic, also now popular, is a great way to spend an hour or two and the views are stunning. There's a good chance you will see some local wildlife too.

Next, onto Yanderra. This is the most southern village of the Dilly and on the very edge of Western Sydney before you enter the Southern Highlands. The highlight here is at the local village centre, KTK Baking Co serving up fresh baked goods, Seven Mile Coffee, and an abundance of country treats. If you’re lucky enough to get one, grab a cinnamon scroll made fresh by pastry chef Katie. This is one of those off-the-beaten-track locations you will want to come back to again and again.

Passing the famous Tennessee Orchard, more old bridges and one very cool Sydney Harbour Bridge vibed modern offering, we leave the dilly and continue just a little south. Tourist Drive 12 has a real sense of being undiscovered as you pass through Yerrinbool, a little village with a quaint character. Stop and check out the cute little community garden at the local railway station.

One last arched bridge, framing the road beautifully, we climb through some green hills, pastures, and landscape to join back onto the Hume. You’ll wonder why you haven’t taken this little drive before!


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