I'm not sure how soon I'll have a base deep enough to take a crack at "the triptych" -- an out and back figure eight sort of thing at Crowder, a boat ramp-campground-17-campground at Indian Creek, and an out-around the loop-and back from Thousand Hills Park -- each roughly around 18miles apiece -- all in a single day.
If I really wanted to put the hurt to myself, I could make it a four course goal called "the four horsemen" and add Sugar Creek to the mix. Sugar Creek, if you ride all of it, is somewhere between 9 &10 miles of rattle your teeth loose horse trail. It's steep and rough and not built with any consideration for sustainability whatsoever. It's a good workout. I still haven't attempted it on the SS. I plan on using it as a guage for when I first dare trying the triptych. I figure when I can "comfortably" double up Sugar Creek and Thousand Hills, then I can start doing both Crowder and Indian Creek when I head over, then eventually start throwing in Thousand Hills on the way back.