Mittagong to Berrima
via Mt Gibraltar and Bowral (24km)
June/July 2026
Words and Photographs Tony Sheffield
THIS DRIVE’S STARTING POINT is Mittagong’s Queen Street, off the Old Hume Highway. Follow this road past many dreamy historic sandstone cottages and Mittagong Library, which was home to Mittagong Public School from 1878 to 1937, when a new school was built nearby. It has been a library since 1941.
Continue down the street to Lake Alexandra, which is great for walks, picnics, feeding ducks and has a good children’s play area. Bear right into Alfred Street then left into Victoria Street climbing all the time for an elevated view of the lake on the left.
Turn left down Arthur Street alongside the lake and return to Queen Street back to the Old Hume Highway and turn left. Mittagong’s theatre, which is being refurbished, is on the right, followed by the memorial clock tower, unveiled in 1920 to honor those who fell in World War I. From here drive north-east on the Old Hume Highway where you can see several of Mittagong’s 19th century buildings including St Stephen’s Anglican Church on the right. The church was completed in 1878 on an acre donated by the Fitzroy Iron Works, Australia’s first iron foundry (its 1850 foundations are preserved in the carpark under the town’s Highlands Marketplace shopping complex).
Head past the church and turn right into Albion Street then left into Regent Street and right onto the railway bridge – you’ll see the old Station Master’s House just before the roundabout. Take the second exit to continue along Range Road. Further along on both sides of Range Road is Frensham School for girls. Turn right into Waverley Parade and immediately on the left is Sturt, Australia’s oldest craft centre, established in 1941. Continue along Waverley Parade, cross Oxford Street and turn left into Oxley Drive to begin the ascent of Mount Gibraltar.
This is a blue ribbon residential area, stretching to Bowral, with Mount Gibraltar Heritage Reserve at its peak. The road twists and turns all the way to the summit of 863m, where there are three lookouts.
After passing the second Duke Street turnoff (the street connects twice with Oxley Drive), turn right to see two of the lookouts. You’ll first reach the Mittagong Lookout from where, on a very clear day you can see the Sydney skyline. Next is Jellore Lookout, a two-minute walk down the track, which looks out to Mount Jellore, the Nattai and Kanangra-Boyd wilderness areas, and the Blue Mountains (a great photo opportunity at sunrise).
On your descent, drive straight ahead at the intersection and shortly after on the right is a turnoff to the Bowral Lookout and picnic area (there are toilets here too). A boardwalk with disabled access leads to a terrific view of Bowral town. Beyond is the Wingecarribee River Valley, Moss Vale, Mount Gingenbullen and the Cuckbundoon Ranges near Goulburn.
There are also walking tracks, including somewhat challenging steps down to the Trachyte Quarries, a heritage-listed former industrial stone quarry, which operated from 1886 to 1986. It produced distinctive grey trachyte and syenite (microsyenite) known as Bowral Trachyte, which was used in major landmarks, including Sydney’s Queen Victoria Building, the NSW State Library and Australia House in London.
Continue along Oxley Drive to the bottom of the mountain passing the Bowral Swimming Centre and turn left onto Mittagong Road leading to Bowral’s centre. Fork right at the lights into Station Street, next to the memorials, and at the next lights turn right to go over the railway bridge and right again into Kirkham Road, passing Bowral railway station, built in 1867.
Continue and turn left into Centennial Road which slowly climbs, passing some very desirable homes, two hotels (The Gibraltar and Peppers Craigieburn) and their two golf courses. Towards the top, on the right, is Centennial Vineyards, a vast estate with a cellar door (open 10am to 5pm seven days) and an excellent restaurant.
Turn left at the end of Centennial Road into the Old Hume Highway towards Berrima. Two kilometres along on the right is Bendooley Estate, run by Paul and Katja Berkelouw, which boasts an impressive restaurant, a cellar door and a book barn with second-hand and new books. Both Centennial Vineyards and Bendooley Estate are popular destinations (and wedding venues) and well worth a visit.
Continue along the highway and turn left into Oxleys Hill Road. This is one of the most picturesque, undulating drives in the Highlands, and there’s another Bowral lookout on the left where you can stop to take in the scenery before the steep descent back into Bowral.
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