If you can catch a train to Tahmoor on the train line to Bowral near Sydney, you can have a great gravity fed ride all the way to Picton on country roads. You need to travel to Campbelltown and swap trains. Check the timetable carefully.
The ride starts at Tahmoor Station and heads west to the Thirlmere Railway Museum. Its shared path and a road or two. All fine. Thirlmere has a couple of eating opportunities and the Railway Museum
If you have a mountain bike head down to Thirlmere lakes and do a lap of the lake. The MTB track on the west side is so easy, I could do it. This detour is probably necessary if you are trying to make a day of the area.
The Country Ride
The best cycling though comes from heading down to Picton. Head down Westbourne to Cedar Creek road where you have an uphill section. Follow Cedar Ck till it ends at Mulhollands Rd and turn right. Watch for Cedar Creek Orchard where you can try some apple juice. Follow Mulhollands Rd all the way downhill to Barkers Lodge Rd. This is a busy enough road with a 6 foot verge. Follow this for 2km and turn left into Abbotsford Rd. Keep going into Fairleys and down to the Picton Showgrounds. All up, this a lovely country ride with little peddling.
You are in Picton, enjoy quite a few kilometres of shared path around Racecourse Creek. And then return and head into town past the fairly lame botanical gardens. These have toilets. In town, there are cafes and the like.
Now cross over Stonequarry Creek on the bridge and head left to Picton Avenue as per my map. At the end (ok there is a hill) there is a small path that crosses the creek way below. To your left you will see the very tall Picton Railway Viaduct. It’s a beauty. Soon after and there is Webster Creek that has a number of historic wooden cottages. The railway station is not far away.
Heading Home When you go to hop on the train, beware that the train does a strange loop though the town so you board on the east side to go north. I stuffed up and nearly headed off to Bowral. Board the train in the middle. Be confident, you will sort out what to do once you are on the train.
Road Warriors. You won’t be doing the mtb track, so start in Picton and head up the hill first to Thirlmere or start in Tahmoor and ride around the roads in that area. You can have a big pie there at the bakery and roll back down to Picton.
22km trip from Tahmoor station to Picton Station.
15km MTB to Thirlmere Lakes
36km for the Road Warriors option