I am sorry not to have heard of this earlier, though I live some of the time in Richmond and work in Penrith. I am not a SUP paddler, but a kayaker. All of my descriptions below are of paddling against the flow.
From the broken rapids at Castlereagh to Emu Heights is 6km of very flat water with no true obstacles.
To paddle upstream from Tench Reserve (under the M4 at Penrith - or, an additional 3km from the rowing club/railway) would take you through 15km of a spectacular quiet gorge that is part of the Blue Mountains National Park on both banks. You can bail at Norton's Basin if you have support or partially walk gravelly shallows to Wallacia, just down from the well-known hotel.
To enter the Grose River is a good thing to do, though the water is ankle-high over golden sand for 1.5km to then enter the Blue Mts - with many 10's of km of rapids above you.
Where the wild Grose meets the Nepean, it changes name to the Hawkesbury.
You can paddle your SUP 2.5km, with no obstructions, up the Warragamba River. Steep-sided bushland. Speccy to see the dam wall rise up in front of you - and you certainly
are not trespassing to be below it.
You can paddle 18km up the Colo River from Lower Portland (locality with good road access). At high tide, you can paddle another 3km to the timber Upper Colo Bridge. Most fun if you can organise to get dropped off - or a car shuttle.
~~~~
Of that photo of the can of
Monster. It is depicted amongst
Salvinia, a fresh water weed that can more than double in area twice a day.
weeds.dpi.nsw.gov.au:443/Weeds/Details/118~~~~
No doubt the Windsor Canoe Club told you of the annual Hawkesbury Canoe Classic held annually in October. 111km overnight.
www.canoeclassic.asn.au/ Several SUPs have completed it now.
www.abbeydigital.com.au/ev/131026HC3/e2/index_3.htm