NSW’s 2026 Small Tourism Town of the Year is also one of its most underrated winter stops. This gold rush-era town in the Mudgee region has a heritage streetscape that genuinely transports you, a thriving food and wine scene, boutique stays and a thriving arts culture. An hour from Mudgee, Gulgong is also known for being the town on the $10 note and the childhood home of legendary Australian bush poet Henry Lawson. gulgong.com.au

Pull on your knee-high boots to better blend in with Bowral locals. Just 90 minutes from Sydney, Bowral is one of the cosiest towns in the Southern Highlands to visit over winter. Enjoy lunch with your Bowral-based benefactor at Three Blue Ducks on the regenerative property, Burradoo Park Farm. Or hunker down at Horderns Restaurant at Ardour Milton Park Bowral, which has had a $10 million transformation. Enjoy lunch at the lovely Lucette and head to Aspinall’s Whisky Lounge for a fireside nightcap. visitsouthernhighlands.com.au

Just three and a half hours northwest of Sydney, Mudgee is a textbook town for a winter weekender. More than 35 cellar doors, destination dining at zin food + wine house on the Lowe Family Wine Co estate and Pipeclay Pumphouse at the Robert Stein Vineyard make this one of NSW’s great regional food towns. On weekends, take a day trip to De Beaurepaire Wines in Rylstone for a tutored tasting in an 1850s sandstone stable that once housed the winner of the Melbourne Cup. visitmudgeeregion.com.au

The best towns to visit in Australia during winter give us an excuse to take our jackets out of mothballs. Seek shelter from the cold in this historic village at the iconic Nundle Woollen Mill where yarns will definitely be spun. Shed a few layers for a pub lunch at the Peel Inn Hotel. Try your hand at fly-fishing at Arc-en Ciel Trout Farm. Complete the cosy circuit with a visit to the historic 1890s Odgers and McClelland Exchange store. nundle.com.au

Murwillumbah is a must as one of the best regional towns for eating and drinking. But temperatures don’t drop to the extreme in the original Art Deco-era town, making it a popular draw for families who want to get their kids out of the house in winter. Pop into The Imperial Hotel for a pub meal, as it has a cosy fireplace to warm up around. Pasta Bah and Kat Harvey Cheese are also warm and inviting eateries to visit in winter. Stay at the Glenelg Murwillumbah if you’re looking for panoramic regional views. visitthetweed.com.au

Wear sensible shoes so you can hit the high street running in Rylstone, on the banks of the Cudgegong River. Rylstone is no stranger to tourists, as its high street is lined with beautiful historic buildings and it’s an easy day trip from Mudgee. Rylstone is also a hot destination in winter thanks to 29 Nine 99 Yum Cha and Tea House, known for its dumplings. Visit De Beaurepaire Wines to taste French-style wine grown on a single-estate vineyard in a charming cellar door that is an 1850s’ sandstone stable. And bunker down at Wollemi Retreat. visitnsw.com

Bundanoon looks like the bucolic ideal of a cosy village in wintertime in the Southern Highlands with its plethora of cutesy cottages and historic buildings. Rug up and follow the heritage trail around Bundanoon, which is known for its Scottish heritage and annual Highland Gathering. Or ramble around the gardens and visit the Glow Worm Glen. When you’re ready to hit the hay, do so at The Pill Factory or Stringy Bark Hut at Wildernest, 20 minutes out of town. visitsouthernhighlands.com.au

A visit to Jugiong is not complete without a jaunt to Jugiong. Jugiong has gained notoriety as somewhat of a haven for foodies heading up or down the Hume Highway between Sydney and Melbourne. The town buttressed by the Great Dividing Range and tucked away in the Riverina’s cattle country is your gateway to the Hilltops region of NSW. But you’re more likely to know it for being home to the 1850s’ hotel, The Sir George. The beautifully restored hotel is a landmark attraction in the charming village where cosy nights and seasonal fare are calling. visitjugiong.com.au

A vacay to Uki in the Tweed Valley during winter will help stave off cabin fever. It’s winter lite. The weather is warm enough to get a sunglasses tan during the day but cool enough to cosy up by the fire at night. The town of Uki keeps things lively with a roster of live entertainment at the cheery Mt Warning Hotel, which boasts views of Wollumbin. The tiny town is also a must-visit spot for those in search of pies and pastries from NSW’s best regional bakeries. Head to Bastion Lane Espresso housed in a 1909 post office for coffee before checking in at Chesson Lodge, which has an open fire and can accommodate four couples. visitthetweed.com.au

You don’t need to be travelling on a sled pulled by huskies to justify wearing woollen gloves and a puffer jacket in Australia. Young, the Cherry Capital of Australia can get pretty chilly. And this is what some of us want so we can get out our ugly Christmas in July jumpers and toast marshmallows around a crackling fire. Yeah, we know. It’s not the Swiss Alps. But the olive groves, orchards, vineyards and heritage architecture all turn up the cosy vibes in this regional NSW town, which is about a four-hour drive southwest of Sydney. Let the misty mornings melt into the afternoon. It’s on for Young and old. visithilltopsregion.com.au

Lilianfels Blue Mountains Resort & Spa has long been a lure for visitors to the Blue Mountains. Now, the 1889 estate overlooking the Jamison Valley has had a multimillion-dollar nip and tuck for its second act as Ardour Lilianfels Blue Mountains. The grand old dame brings The Lounge bar, caviar service and a new culinary direction to one of the mountains’ most storied addresses. Beyond the estate, Tempus does seasonally driven plates in a converted heritage bank and Avalon’s Friday Supper Club will warm the cockles with live jazz and winter share plates. visitbluemountains.com.au

You don’t need to be reminded to look up on the main street of Sawtell: the giant outstretched arms of the fig trees give a lot of main-character energy on the sleepy strip. Enjoy this dramatic backdrop when you pull up a stool at Bar Que Sera, where it’s more a-la carte than whatever will be will be. Follow your nose to the Palmetto food van for a pulled pork roll and The Spare Room to listen to live music. The annual Sawtell Chilli Festival is the place to go for a Coffs Coast vibe-check. coffscoast.com.au

Australia’s second oldest river port has a lot of unexpected surprises. The beautifully preserved main street of Morpeth is still regarded as Maitland’s prettiest pocket. Mooch along the Hunter River in Morpeth to admire some of the historic buildings that saw the town classified by the National Trust. Find a perch at Common Grounds to meet Morpeth locals. For dinner, Boydells delivers wine flights and small plates in a warm, cosy room that is housed in a historic slab hat. Stay at the Bronte Boutique Hotel and wake up to a thick mist veiling the river. itmustbemorpeth.com.au

Everything is amplified during the cooler months on NSW’s South Coast from the painted-on blue skies to cosy pubs with fireplaces like The Milton Hotel to combat the frosty weather. Sit on the sun-dappled terrace for comfort food like wagyu beef short rib with slaw and sesame crumb. The Milk Haus in nearby Woodstock is also a must for seasonal produce and hosts regular Fire + Feast nights in winter. Milton’s weekly farmers’ market is also a must for seasonal bounty. Book a stay at Cupitt’s Estate, one of the best farm stays in Australia for foodies. visitnsw.com

Go on. We dare you to travel along the road to Gundagai without belting out the lyrics to this famous Slim Dusty song. Just minutes off the Hume Highway between Sydney and Melbourne, Gundagai still stops road-trippers in their tracks. The sandstone streetscape, the famous Dog on the Tucker Box and the lookout above the Murrumbidgee River are all worth your time. Flash Jacks is the go-to for a pub feed and local conversation. A low-key, genuinely warm stop with enough charm to strong-arm you into staying longer than you planned. visitgundagai.com.au