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Here’s The Perfect Long Weekend Itinerary From Sydney To Orange, Featuring A Lot Of Wine

Here’s The Perfect Long Weekend Itinerary From Sydney To Orange, Featuring A Lot Of Wine

In 2021, I’m really starting to perfect the art of the weekend road trip. It’s not about the destination as much as it is about the journey because, after all, you only have two to three days and you don’t want to spend all of them driving.

Recently, I took a trip out from Sydney to Orange — which somehow became an absolutely country haven for amazing food and lush vineyards. I’m quite confident I’ve managed to perfect this road trip itinerary, so please enjoy.

Day 1

9.00am: Drive from Sydney to Lidsdale

Drive: 2 hours


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What’s in Lidsdale, you ask? I don’t have the words to accurately describe the experience that is Jannei Goat Dairy. Obviously this one is for the cheese lovers, considering this small farm has one several awards for their varieties of goats cheese.

It’s also just absolutely the quirkiest small country town experience I’ve ever had. Janette — one half of the married-couple team that runs the dairy — sits us down for a tasting, and the woman has STORIES. She knows it too, she’ll tell you herself she never stops talking but it’s in the most delightful way.

From the stupidly good cheese, to the very unique family portrait on the wall of the tasting room, to the adorable goats Janette was kind enough to show me — this is an easy half hour stop that you won’t forget any time soon.

11.30am: Detour to Capertree

Drive: 20 minutes

This is a little bit of a detour to your final destination, but if you love whiskey, it’s absolutely worth the 20-minute drive.

Craft Works Distillery is a little tin shed out the back of a rustic country pub — run entirely by Craig “Crafty” Field, mills — brews, distils, barrels and crafts their own single malt whisky, Australian style. Let me just tell you, I do not like whiskey (although I do enjoy gin, which Crafty also dabbles in) but just half an hour with this guy and his absolutely enthusiasm for what he does has me wanting to know more. It’s kind of like what would you expect if your dad said ‘screw it’ and turned the garage into a distillery — except that if was actually really good at it.

Not to mention his daughter (who’s age I can’t entirely remember, but was about 10) designs a lot of his bottle labels and they’re actually very cool.

1.00pm: Take a lunch break in Bathurst

Drive: 1 hour

I know, I know, Bathurst? Yes, Bathurst. In 2020, this town experienced one of the biggest YOY holiday booking growths in the country. You won’t be staying the night this time, but you will be stopping for lunch at the extremely cute Church Bar. The vine-strewn courtyard is absolutely adorable, and the perfect place to stretch your legs and enjoy some some.

4.00pm: Continue on to Orange

Drive: 45 minutes

You absolutely have to stay at Byng Street Boutique Hotel in Orange. What used to be an old homestead built in 1896, the interior received an upgrade while the original exterior remained the same. Half the hotel is in the historic building, and the other half was added on. Having stayed in both halves, I strongly recommend asking for the heritage wing.

Beyond how adorable it is, the hotel is also in the perfect central location. It’s a walk or short cab ride to nearly everywhere in town, which means you can have a few drinks with dinner and not have to worry about driving yourself home.

Tonight, I highly recommend dinner at Charred Kitchen & Bar. Frankly, the website didn’t do the place any favours so I honestly was not prepared for how delicious the food is (sorry Orange, I’ll never make assumptions again) and the focus on local produce just makes it even better — because who doesn’t want to support local.

I went for the four-course degustation, with matching wines obviously, and honestly if you’re not doing the same then you’re not doing it right. I don’t eat meat so I stuck with the vegetarian menu, and it’s one of those places where you definitely don’t feel like you’re missing out. The sommelier was super enthusiastic and stuck to wines form the Orange region so we could get a literal taste of everything on offer.

Day 2

10.00am: Start the day right

Drive: 7 minutes

Everyone who skips breakfast is insane, it’s clearly the best meal of the day — and essential if you’re going to make it through the glorious day of wine tasting you’re about embark on.

One of the cutest options you’ll find (and the absolute best chai lattes ever), is The Agrestic Grocer. Again, they focus on local and ethical produce, which they create into amazing and very creative meals. They also have a grocer next door, and live music on Tuesday nights.

11.00am: Wine about it

Drive: All day, but make someone else do it.


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I honestly can’t tell you when it happened, but Orange is a wine region to rival all others now — which makes today the perfect excuse to go sample them all. I was lucky enough to have a private driver, but honestly pick a wine tour, any wine tour.

Some highlights for me were Ross Hill Winery, having Rowlee Wines set up the most gorgeous picnic basket that I then got to devour with beautiful views of their vineyard, and stopping in to pick my own cherries at Hillside Harvest.

If you like beer, you absolutely have to get out to Pioneer Brewery too. Seemingly in the middle of nowhere, Pete Gerber used his skills as a mechanical engineer and his extensive experience tasting beer around the world to start his own family-owned brewery. Make sure you have a ride home, because you are absolutely here for the tasting flight.

7.00pm: Save room for dinner

Drive: Hell no, just a short walk.


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I’m not going to lie, you’re probably going to be too drunk and full to even fathom dinner, but just in case you have a little bit left in you, it’s worth the effort to waddle from your hotel to The Schoolhouse Restaurant at The Union Bank (yes, it’s actually within walking distance).

Their menu focuses on what local produce is in season, and they just make damn good food. My only regret is not being hungrier so I could eat more.

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Day 3

10.00am: Nurse your hangover with brunch

Drive: 1 minute


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No one could blame you for ordering breakfast to your room (Byng Street Hotel has a fab menu), but if you feel up to getting out of bed after a little sleep in there are a few brekkie places around town, like Birdie Noshery & Drinking Est, where the interior is pretty dang cute.

11.30pm: Hit the road to Lithgow

Drive: 1.5 hours


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I was surprised too, but there’s more than just a black panther to find in Lithgow. The Blue Fox Bar & Kitchen is an absolute gem for a lunch break. It’s a family owned and run restaurant inside a fully renovated and very beautiful old home.

If you’re feeling more of a grab and go vibe, the same owners have a takeaway store for more casual eats right next door.

2.30pm: Take the scenic route

Drive: 45 minutes


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From Lithgow, you’re going to follow the Bells Line of Road. Despite dealing with the smoke from the 2019/20 fires, this was the first time I really saw up close just how much damage they’d caused. The view along this road is striking and deeply intense but still beautiful, especially now regeneration has started.

All the more reason to keep exploring these areas and supporting local communities.

Don’t stop until you hit Bilpin and the rustic haven of Hillbilly Cider Shed. Stay for a tasting of their locally made ciders — including their international award winners. The smells wafting from their wood fire pizza oven was absolutely calling me too, so I recommend making this the lunch spot if you want to skip Lithgow.

4.00pm: Head home

Drive: 1.5 hours


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Trust me, by now you’re tired and very full, but it was totally worth it. Time to head back to Sydney and probably not be able to eat for a few days.

The author travelled as a guest of  Tourism Australia.

(Lead Image: Provided by author)

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