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Lucky Legs run
From the Mittagong side of Bowral Bowral get to Old South Road (v.easy to find), follow in northly direction towards Mittagong via a huge, huge hill to where Old South Road meets Range Road (crossroad); distance would be 5km or 6 depending on starting point.
Turn right into Range Road & follow it (up & down hills) out to Glenquarry village; there's a tiny, old, white church at the junction of Range Road & Tourist Rd/Macquarie Pass; distance for this section would be around 9km. "T" section here & Range Road ends.
At Glenquarry, go left & follow Tourist Road downhill for about 3 kms of winding road (fantastic views from the top of the ranges here! Watch out for the few cars, bikes on the hair-pin bends!.
I've driven each km from here on : they are approximately! ... 2km to a property on the left called " Quarryglen "; 1km to a polo field on right; 1km to a lane called " Yoe's Road " on right; 1km to next lane on right called " Jack Emery Lane "; 2kms to an old bridge where a sign says " Bridge Road "; 1km to " Crest " sign; 1km more to an "80km" speed sign; ; the next 3 kms you might not see as I've marked each with a slash of cream paint on both sides of the road! then 1km further to a property on your left called " The Dawn "..i.e. 13km for this section. Beautiful, quiet countryside!
So, leaving out the few kms from Bowral to Mittagong, this run would be 22km out, very approx.!! Turn around at any stage on Tourist Road in order to do the length of run you want or.. if you keep running you'll reach Robertson & eventually the coast at either Wollongong or Nowra!!
There are many, many more fabulous places to run here, however, any road out of Bowral to anywhere, would give you a good run with fantastic Autumn colours!
One of my favourites is to run from Bowral out towards Berrima (a beautiful little village! Wherever you run, you will enjoy!!) on either Centennial Rd or Oxley Hill Rd (West), turn left at the Old Hume Hwy and out through Berrima. Then come back through Taylors Ave / Berrima Rd into Moss Vale, and then back to Bowral via the cyclepath they have recently built between Moss Vale and Bowral.
But it also seems a waste to run on the roads when there is so much great bush around the Southern Highlands.
You could also take a drive down to Fitzroy Falls (15-20 mins) and just head out on some of the trails for an hour, then turn around and come back.
Wingecarribee Bush Runners
if you are around on a Sunday morning, and you want some company, you could meet up with the Wingecarribee Bush Runners, who meet at a different spot at 7.20am every Sunday and run in some of the best scenery you will see. They are an eclectic group, with all standards of running. They often have people joining them from Sydney who are down for the day. They run anywhere from 10-24kms at a time. You can find out where they run in the local paper every Wed or Fri (in the Sport classifieds under Athletics)
Cragieburn and Mt Gibraltar
Go out of Cragieburn turn right go up to the Old Hume Highway turn left down the steep Hill and then as you start to go up the other side there is Berkelouws on the right - buy a book or at the very least get a drink. Go up the hill and near the top is the other turn left and head off off back to Bowral. The Bowral Ironmen triathletes train on this circuit.
Go down Oxley Hill and you are on the western side of the railway line. I would then run over the railway turn left (have a drink) and head down the main road past the pool and take the first right. This will take you to the top of Mt Gibraltar. If you are really keen you can go down the other side to Mittagong and come back or turnaround at the top and just return to Craigieburn.
I was trying to work out the distances but it is shorter up the Craigieburn road maybe 4km from the railway line, 3-4km along the Hume Highway, probably 6km ( not sure with this leg?) from the Hume Highway down Oxley Hill to railway line again. From the railway bridge to the top of Mt Gibraltar would be 3km and 4 and a bit back.