Cycling the Southern Highlands
The Southern Highlands is road cycling at its most civilised. Quiet country lanes wind between historic villages, grand estates, vineyards and green paddocks, with a bakery or café never far away. Sitting 600–800 metres above sea level, the Highlands is cooler than the coast — perfect for summer riding — and only 90 minutes from Sydney.
Our guides cover the classic loops from Bowral and Moss Vale, the rainforest roads around Kangaloon and Robertson, and the escarpment drop to Kangaroo Valley.
Cycling the Southern Highlands: road rides around Bowral, Moss Vale and Berrima
Why ride the Southern Highlands
Quiet back roads. Most loops follow sealed country lanes with light traffic.
Village hopping. Bowral, Mittagong, Berrima, Moss Vale, Burrawang and Robertson are all within easy riding distance of each other.
Cool climate. Summer temperatures are often several degrees below Sydney and the coast.
Food and wine. Cellar doors, bakeries and country pubs make perfect ride stops.
Coast-to-highlands combos. Link up with Illawarra rides via Macquarie Pass or Jamberoo Mountain for a big day out.
Things to know before you ride
Cold mornings: frosts are common from May to September. Start later and pack gloves, arm warmers and a jacket.
Fog: Robertson and Kangaloon can be thick with fog. Run front and rear lights all day.
Road surfaces: some country roads are coarse chip-seal with edge breaks. Run 28 mm tyres or wider.
Trucks: the Illawarra Highway and Moss Vale Road carry heavy vehicles. Use our quieter back-road routes.
Train access: Bowral, Moss Vale and Mittagong are on the Southern Highlands Line.