At 650 to 860 metres above sea level, the cooler inland region of the Upper South Coast is known as the Southern Highlands. Gorgeous highland towns lie surrounded by English like countryside just off the Hume Freeway, the major highway heading south out of Sydney. The alternative and far more scenic way into these rural communities is via the various routes which stem from the coast.

The best of these is the route from Nowra which passes through the breathtaking Kangaroo Valley. This historic valley is a collection of lush rolling pastures backed by steep rainforested slopes of a sandstone escarpment. The beauty and tranquillity of the area is deservably popular for the many B&B and camping retreats. The village itself is home to some lovely old sandstone buildings, several art and antique stores, some places to eat, and a friendly pub. There's also Australia's oldest suspension bridge on the western edge of town.

Further inland the road passes through the northern finger of the huge Morton National Park and the spectacular Fitzroy Falls. The falls plunge more than 80 metres over the sandstone cliffs into the rainforest of the Yarrunga Valley. There's an excellent visitors centre in the nearby township which can help organise walks to the other falls in the area. Also in town, the Fitzroy Gallery specialises in unusual pottery.

The journey ends at the hub of a small road network in the historic highlands town of Moss Vale. As quaint as it sounds, the agricultural centre of the region is brimming with gracious old buildings, preserving the towns heritage and accurately reflecting early rural lifestyles. A popular retreat for Sydneysiders seeking solace and antiques.

South-west of Moss Vale, Bundanoon is renowned for it's views over the rugged mountains and gorges of the northern stretches of Morton National Park. This particularly scenic section of the park has some fine walks, breathtaking lookouts, and the famous glow worms visible at night in Glow Worm Glen. Bundanoon itself is a beautiful town boasting quality food and accommodation, a collection of galleries and studios, an English pub, and a health resort. Renting a push bike from Ye Olde Bicycle Shop is the traditional and best way to get around. Every April competitors, pipe bands, and spectators merge on the area from all over the country for Brigadoon, the largest Scottish Highland gathering in Australia. Traditional games include caber tossing and haggis hurling.

To the north of Bundanoon and Moss Vale, the charming towns of Berrima and Bowral have been most successful in retaining their historical grandeur. Berrima is famous for its Georgian buildings as well as the art and craft galleries and antique stores which consume the streets. Bowral's main attraction is the Don Bradman Museum, a tribute to Australia's most enduring sportsman. The community also hosts Tulip Time in September/October and co-hosts the annual Shakespeare Festival with Mittagong in March.

The Gateway to the Southern Highlands, Mittagong is graced by some more lovely old buildings and keeping within flavour of the region, a number of craft and antique centres. On the outer edges, Lake Alexandra attracts a profusion of friendly birdlife and is an ideal place to unwind with a picnic.

Further north and not far from the outer suburbs of Sydney, Picton is an easily accessible escape from the bustle of city life. Settled in 1822, the old buildings and quiet hills of this gorgeous country village are evocative of an earlier era. The splendid railway viaduct at the end of town is a bold indication of it's colonial heritage. Visitor's gather in Picton's centre to browse through the many art, antique, and gift shops and to sample Borrogarang Bock at the fabulous George IV Hotel.