Cycling in Sydney Australia
Probably always a tradeoff between directness and fast traffic on the main highways and lower trafficked parallel roads, eg Federal Highway and Monaro Highway v back road via Bungendore and Captains Flat, or Goulburn/Braidwood/Berlang, which has very little in way of civilization- youd have to be self sufficient.
Monaro Highway is notorious after death of long distance cyclist Mike Hall. A lot of it has a narrow shoulder, say about 0.5 m, so youd have to be OK with being close to fast traffic, and very cautious at bridges and places where the shoulder cuts out or is restricted by barriers etc, but it would be much faster than alternatives.
M7 cycleway to Prestons.
Camden Way cycleway to Camden
Cawdor Rd to Razorback then Remembrance Dr into Picton
Picton to Mittagong (via Thirlmere) Wilson Dr
Mittagong to Moss Vale via Old South Road/Moss Vale Rd
Moss Vale to Marulan via Exeter Highland Way
Marulan to Tarago via Oallen Ford Road / Cullulla Road
Tarago to Bungendore via Tarago Road
Bungendore to Canberra/Queanbeyan via Hoskinstown Rd / Captains Flat road
These were all fairly quiet roads (at least on weekends) with reasonable distances between civilization.
Can't help south of Canberra. I don't do hills gov ;)
You might want to have a look at this trip that I did a few years ago. It won't get you to Perisher, but it'll cover a lot of the route you'd need to use. This was an enjoyable but tough ride, particularly Bathurst > Hill End > Mudgee > Kandos > Lithgow.
If you're pressed for time, I'd suggest catching the train from Sydneeeee to Goulburn and riding from there. It's not necessary to box your bike if you use ShittyRail or whatever they call themselves these days.
Warren Hudson rates the Braidwood to Cooma via Berlang (Snowball) road highly for its wilderness. Or the Jerangle Rd is a bit more civilised. Check Warren’s posts on SC, too, he has some great photos of rides around Canberra and Yass. https://www.bicycles.net.au/forums/viewtopic.php?t=43987