Set off early from Canberra and head north on the Hume and Barton Highways with a refreshing first stop at Boorowa for a coffee and a wander through its heritage main street; try a pastry at a local bakery and stretch your legs at Boorowa Lookout for sweeping valley views. Continue via the pastoral backroads to Young where you can visit a roadside orchard stall for fresh stone fruit (season permitting) and take a short detour to the serene Garema Reserve for a quick picnic before resuming the scenic drive toward Rutherglen.
After your Young stop, continue north and arrive in Gundagai for lunch-grab a table at a local pub or café and stroll to the iconic Dog on the Tuckerbox for a quick photo and riverside views of the Murrumbidgee. In the late afternoon, detour through rolling countryside to Holbrook, where you can explore the fascinating Submarine Museum and relax with a walk along the leafy main street before driving the final stretch toward Rutherglen as the light softens.
As daylight fades, settle into Rutherglen with a leisurely tasting at All Saints Estate, where you can enjoy a guided flight of fortifieds and a stroll through the historic cellars. Afterwards, dine at The Wine & Food Garden (or another local bistro) for regional cuisine paired with Rutherglen wines, then finish the night with a relaxed walk along the tree-lined streets to take in the town's mellow evening atmosphere.