A scenic three-hour drive from Sydney, and an hour from Canberra, Yass Valley is at the heart of the cool climate Canberra Wine Region. Vineyards thrive within Yass’s historic country estates, marking the delicious start of this heritage tour with something sippable.

Savour a shiraz viognier at Clonakilla Wines, surrounded by local stone and reclaimed timber. At Shaw Wines you’ll taste award-winning reserves in a 19th century wool-producing property.

Helm Wines is based in a heritage schoolhouse once used for meetings by the Temperance League and now specialises in reisling. Tallagandra Wines and Dionysus Winery both produce premium wines of unique regional flavour.

Tuck in to country flavours with smoked duck breast and a pinot noir at Poachers Pantry Smokehouse Restaurant and Wily Trout Vineyard. In the refurbished 1865 Royal Hotel in Gundaroo, Grazing is an acclaimed fine-dining experience. You can also dine among the grapes at Four Winds Vineyard’s casual pizzeria, where the views are as stunning as the wood-fired pizzas and wines on offer.

Finish off with chocolates from Murrumbateman Chocolate Co, made handmade with fairtrade cocoa from the Caribbean and Latin America.

Be a part of the region’s inspirational stories by shopping for exquisitely crafted local wares at Creators Nest – you can also join a workshop. Explore the colourful mosaic garden at Tootsie, a wonderful gallery and cafe set in an historic Art Deco garage.

Wrapped in yellow canola fields, the drive to the twins towns of Harden and Murrumburrah ushers you into a region brimming with well-preserved colonial architecture and gold rush legends. A gateway to surrounding touring trails and heritage-listed attractions, you’ll also find antiques, vintage pubs and delicious local delights.

Take a low gear through the surrounding fields on the Antique Trail, a touring route that explores the Hilltops region where gold miners, bushrangers (including the famous Ben Hall) and troopers once capered. Along the way, you’ll find antique shops filled with local treasures, pubs and the Elizabethan-style Iandra Castle, an hour north.

The museum also brings the past to life with historic artefacts such as a blacksmith forge. Visit the the information centre and discover more attractions. Relax in a rustic courtyard with one of Jackson’s Bakery’s famous pies and a coffee. The nearby Light Horse Memorial commemorates the birthplace of the First Australian Light Horse at Murrumburrah in 1897.

Bursting with character (and delicious stone-fruit), a drive through the orchards and vineyards surrounding Young’s gold-heritage heart shows you why this is an essential stopover. Famous for cherries that have thrived in rich soil for over 150 years, the land here will treat you well.

Take a bite of delicious handpicked stone fruit at Valley Fresh Cherries and Stone Fruit. At Ballinaclash Orchard and Cellar Door, pick your own fruit before sampling their wine and cherry reserves. Wine-lovers can visit Grove Estate Wines for a taste of award-winning shiraz. The Information Centre also sells local delicacies and wine.

Tuck into fresh pastries, sweets and savoury delights at local favourite Wilders Bakery before visiting the memorable Lambing Flat Museum, a doorway into the town’s eventful gold rush years, including the infamous Lambing Flat Riot. The historic Clifton House and Gardens homestead delivers the perfect luxury farmstay for those looking for extra comfort.

Winding through the evergreen blooms of Cootamundra wattle, this drive takes you into the cream of country living – the town where cricketing legend Don Bradman was born and where rolling farmland nourishes an area rich with history, theatre and galleries.

Step inside Bradman’s Birthplace, the lovingly restored cottage where ‘Granny Scholz’ ran a small private hospital in the front room, the birthplace of the famed cricketer in 1908. Next door’s Memorabilia Cottage is filled with artefacts dating back to the era. Stroll Captains’ Walk, lined with 42 bronze sculptures of Australian Test Cricket Captains, along with Unaarrimim the first Aboriginal cricketer to tour England in 1868.

Visit the Information Centre and Heritage Centre inside an historic barracks building where you’ll find more artefacts and photos, including a number of exhibition galleries and a locally built motorcycle from 1912. Cootamundra Bird Walk is a lovely amble by Muttama Creek past sculptures of wildlife.

Under an hours’ drive from Young, this part of the drive draws you further into gold rush territory, with historic fighter jets and railway heritage adding to the fascinating story. Proud of its rich history, Temora’s live shows and immersive exhibits welcome you into a vivid and living past.

History takes wing at the Temora Aviation Museum, home to flight displays and one of the world’s best collections of historic aircraft, from Spitfires to a Gloster Meteor F.8.

Wind back time at Ariah Park, a 1920s heritage village with working shops, and grab a drink at the restored Ariah Park Hotel.

The Temora Rural Museum, part of the heritage precinct at Bundawarrah Centre Cultural Precinct, will transport you back to Temora’s past, with exhibits including memorabilia of noted boxing promoter and showman Jimmy Sharman and a fire station. Ever heard the story of Boofhead the Dog? Visit Temora Railway Museum to hear more.

Built during the construction of the Great Southern Railway, the drive to old-fashioned Junee offers a window into a charming bygone era of railway roundhouses and colonial architecture. You can also enjoy gorgeous produce served in heritage settings.

Self-guided tours delve into the region's past, from walks that tell the story of Junee’s railway origins to scenic driving routes. Step inside the awesome Junee Roundhouse, opened in 1947 as the largest roundhouse in the Southern Hemisphere.

Give your tastebuds a tour of the Junee Licorice and Chocolate Factory, nestled inside the old flour mill. Little Rustic Pantry also serves delicious coffee and cakes. Thirty minutes from Junee, you’ll taste award-winning cheeses at Coolamon Cheese and the Coolamon Fire Museum is packed with fascinating firefighting memorabilia.

Arriving at the heart of the Riverina’s famous food-bowl, you’ll discover why the historic vineyards and fruit groves put Wagga Wagga on the map, and this heritage town is a fine place to enjoy the bounty of pleasure that the land yields.

Savour a celebrated dining experience at The Charles. Or learn some tasty secrets at the Food I Am cooking school.

Sip a cocktail at Bar Olivette, an underground speakeasy, or drink in the landscape with some fine wine – or a Tuckerbox Hoppy Lager beer – at Borambola Wines.

Explore the area’s significant past by following the ancient footsteps of the Wiradjuri people with Bundyi Cultural Tours. The impressive Wagga Wagga Art Gallery also holds many stories, with art from across the Riverina, as well as national and international exhibitions. Visit the RAAF Heritage Centre and marvel at their retired aircraft collection. If you'd prefer to get active, explore the Murrumbidgee River, either taking a dip from Wagga Beach or hiring a kayak from In Motion Fitness, which also offers guided tours along the waterway.

Drive through the rolling countryside of the Riverina for a comfortable night in Gundagai, a vibrant and historic town that retains the broad streets and heritage frontages of yesteryear. This is a great base to explore some well-preserved historic trails and treasures.

Stop at the famous Dog on the Tucker Box (and grab a refreshment at the Lolly Shop) on your way in – this iconic monument has been drawing travellers since 1920. You can also reach iton a 4.6km walking and cycling trail that connects to the town.

Spend the morning exploring the colonial heritage of the town, including the Old Gundagai Gaol and Rusconi’s Marble Masterpiece, on the Heritage Walk. Another walk takes you to the impressive historic bridges of Gundagai, whose wooden lattice-works span the Murrumbidgee Flats.

The final stop on this drive through time is the historic village of Jugiong, 20min from Gundagai and on the banks of the mighty Murrumbidgee River. Frequently called the gateway to the Hilltops Region, this town is a great place to take stock of your journey – and to stock up on premium country flavour.

By the banks of the river, the heart of the town resides in The Sir George hotel, built in 1852. This sandstone landmark perfectly captures the meeting of old and new, with a refurbished glory that includes a restaurant, bar, artisan bakery and accommodation.

The Long Track Pantry is another celebrated venue for country cooking and even offers classic cooking classes.

Ever taken a guided tour with a bushranger? Now’s your chance. Follow an outlaw tour guide with the Jugiong Country Experience, and visit the historic buildings along the Murrumbidgee River – including the bush school that famous cricketer and commentator Richie Benaud attended.