How to have a perfect three-day escape in Orange

Loosen your belt a notch and be prepared to indulge in some of NSW’s best food and wine offerings as you explore Orange on this three-day itinerary.

DAY ONE

Morning

While there is a train service from Sydney as well as regional flights with Qantas and Rex, the majority of weekend visitors to this pretty, high-altitude city in the Central Ranges of NSW drive via the Blue Mountains or Bells Line of Road, a 3½-hour commitment either way.

The annual Orange FOOD Week – Australia’s longest-running regional food festival, held over 10 days under a canopy of autumn leaves – is a popular drawcard, with more than 100 themed events celebrating the region’s incredible produce, farmers, winemakers and chefs. But regardless of when you visit, gird your loins for a gluttonous binge, with some of NSW’s most exciting regional restaurants as well as trophy-winning cellar doors contributing to Orange’s reputation as one of Australia’s top wine regions.

Afternoon

Commence your moveable feast at Fiorini’s Osteria, an Orange institution since 2007 when the kitchen, located in a rustic shack on a quiet rural laneway, was in the hands of Italian ‘nonna’ Patrizia Fiorini. Now owned by her niece Kelly and helmed by chef Simonn Hawke (of Lolli Redini and Birdie fame), Fiorini’s has entered a new era where Hawke’s contemporary sensibilities and love of seasonal produce are complemented by long-standing Roman traditions and an unpretentious ambience so beloved by the restaurant’s loyal following.

As you head back towards Orange CBD, swing by the bluestone tasting room of a label synonymous with the Orange wine story, Philip Shaw Wines. One of Australia’s most renowned winemakers, Shaw first recognised the potential of Orange’s cool climate and rich volcanic soils for grape-growing back in 1988, pioneering a region that now boasts more than 60 wineries. Passing ownership of the eponymous label to his sons Daniel and Damian in 2015, 78-year-old Shaw now focuses on his passion project – the handcrafted, small batch label Hoosegg, based at his original vineyard Koomooloo (tastings personally overseen by Shaw are by appointment only).

Evening

Delve deeper into Orange’s history at Yallungah Boutique Hotel on glamorous Byng Street in the centre of town. Built in 1896 as a stately family home, it now features 22 rooms, from the signature suite in the heritage wing to contemporary rooms in the back extension, all amalgamated by contemporary design (colour block, anyone?) and an impressive collection of modern art.

Take a one-block stroll to the Union Bank and its SMH Good Food Guide hat-awarded Schoolhouse Restaurant, or head to another Orange hatted restaurant overlooking the vines at Printhie Wines. Offering a four-course degustation menu, the focus here is on hyper-local and regional fare, with herbs and vegetables foraged from the garden, orchard and forest, and vinegars made from native botanicals. Its specialty is Sydney Rock Oysters, transported daily from the South Coast and kept fresh in a custom-built tank before being shucked to order, the perfect accompaniment to Printhie’s award-winning sparkling wines.

DAY TWO

Morning

Yallungah’s delicious in-house breakfast is worth staying in for, or queue for the legendary French-style butter pastries at Racine, now moved to a new location in Orange Arcade next to Harris Farm Markets. Orange’s vibrant retail scene is thriving, spearheaded by home and lifestyle store Jumbled, a lolly-hued concoction of clothing, tableware, bedding, artworks and eclectic furnishings housed in a former masonic lodge. Linger for a coffee at the in-house Nimrod Cafe, before browsing the fashion at Hawkes General Store further up Sale Street. Dirty Jane’s is the most recent addition to Orange’s streetscape, its tantalising collections of antique and retro furniture, local art and homewares presented in a cavernous building on Byng Street reminiscent of its Bowral sibling. Continue onto the Orange cultural and museum precinct for lunch at Groundstone, a cafe focused on supporting local farmers and producers.

Afternoon

Three out of the six finalists in 2025’s coveted Halliday Dark Horse Winery awards - celebrating producers who have ascended to 5-star winery status for the first time – came from the Orange region, with the trophy awarded to ChaLou Wines. Take a behind-the-scenes tour of this innovative ‘bud to bottle’ winery with young winemakers Steve Mobbs and Nadja Wallington, sampling wines straight from the barrel and delving into their unconventional practices before tasting their range at the cellar door, grazing on a platter of local cheeses and charcuterie.

Evening

After an afternoon of fine wine, a casual meal is in order, with the iconic Hotel Canobolas serving what is widely considered the best wood-fired pizza in town. To round off the night, wander down the street to another ‘local secret’ and newest Guide hat recipient – the much-lauded Hey Rosey, a 20-seater hole-in-the-wall bar that serves wine by the glass, spritzes and cheeky cocktails alongside delectable small share plates (think anchovies on toast, or egg with oeuf mayonnaise) whipped up behind the bar by head chef Hugh Piper, as well as a selection of tinned fish imported from Spain.

DAY THREE

Morning

Clear your head and walk off those added kilos at pretty Lake Canobolas, where a flat 2.4-kilometre track meanders along the shoreline. Especially beautiful under a canopy of autumn leaves, this man-made reservoir is where locals come to walk their dogs, swim, kayak and dragon boat, with a lakeside cafe rounding out the experience.

A short drive from the lake, Canobolas Wines has a stylish new cellar door overlooking an organic vineyard, stocked with an elegant range of lo-fi drops. Further down the road, find one of the latest restaurants to grace an Orange vineyard, Rowlee Dining and Bar. Filling that all-important niche of an elevated dining experience while wine tasting, it offers a seasonal menu showcasing produce from local growers Nashdale, Little Big Dairy, Robanco Meats and Rowlee’s own Block 11 Organics, creatively plated by head chef Simon Furley and paired with the boutique label’s stunning Single Vineyard range.

Afternoon

After picking up a bottle or two of Rowlee’s aromatic and complex pinot gris at the cellar door, head down the road to See Saw Wine for one final tasting. Awarded Best Organic Wine in NSW three years in a row, this certified organic and vegan vineyard, nurtured using sustainable viticulture, is best known for its pinot noir and rosé, while they also make the region’s only prosecco. As this is your last stop on your wine odyssey, load up the boot of your car with these exceptional drops, a taste of Orange worth cellaring.

The writer was a guest of Orange FOOD Week and Yallungah Boutique Hotel.