FATS will be too hard for her, I'm sure, though I would like to get back there soon (I helped work on the trail, then was there for the grand opening 5 years ago).
I just got back from Cypress Trail and... it's still poorly marked. I started out from Dillon Park, went up along the golf course, crossed N Wise, made my way up that field by BD, then crossed Jefferson Rd. I was following the trail and then crossed a small bridge and kept going straight on a high bank that followed a creek. I saw a lady walking 4 or 5 dogs and she said, "Oh, I was trying to get away from you guys", which indicated to me that there was at least one other biker that had come through there (though I saw none). A hundred yards more, or so, and the trail (if you could even call it that) just seemed to end. I'll keep the story short and just say that I ended up having to push my bike through a half-mile of briars, vines, and thicket (in hindsight I should have just turned around and went back the way I came, but I thought I had found the trail again... I think it was just a deer trail) before I found some ATV tracks that led me to a dirt road by a firing range. I followed that back towards Jefferson, and that got me back on the Cypress Trail.
I probably should have hung a right coming off that bridge, but I couldn't tell that at the time and didn't see any indication that I should.
Also, when I was on the trail, I rode up through Cypress Park and then went up and around where it comes out on Airport Rd. There was a sign for the Cypress Trail affixed to a fence post that seemed to direct me left/North, but as I rode through that grass along the road, there were no more signs of the trail continuing. I turned around and followed the trail back to Dillon Park (this time without getting lost in the woods...). If turning around at that point is the intention, then I think it should be labeled as such so that we're not wandering around looking for where it picks back up again.
I talked to some fella at Dillon while I was loading my bike up and he said it actually loops around the back of the golf course, but how would one know that?