Pros:
One starts off with two bombing holes; this is quite welcoming. They both are short par 4s, but it's encouraging. Then you go into the woods with a number of short holes, some of which have distinct elevation (nos. 5, 6; no. 11 on the B9). At no. 7, you come back out into the open; stay in the open for no. 8; but then go back into the woods (briefly) for the drive and approach to no. 9's basket in a small open green. You are briefly back in the open at no. 10, but nos. 11-15 are in the woods. No. 12 fairway is open but does have a ceiling. There is some openness to no. 13, and none of these fairways are without gaps. Back out in the open for no. 16 (tees in the woods). Numbers 17 and 18 either start out in the open and go into a cove or start in a cove and go out into the open. The mix of open and wooded holes is balanced and spaced well. Sherando was something else before becoming a disc golf course (maybe a par-3 9-hole ball golf course?). The difficulty of the holes varies as well. The testers are nos. 5, 6 tee, 7 approach, 9 tee, 11 tee, 14, 15, 17 green, 18 tee.
Cons:
There are no benches anywhere. Understandable for some of the cramped holes, but perhaps there could be a bench at nos. 2/8 and another in the woods (no. 14). In summer, the grass is a bit buggy. Apply DEET etc beforehand. It's very easy to confuse the X hole with no. 12. Next-tee arrows would be useful to help with this. Udisc should help, and there is a picture of the course map (same as what is online here at DGCR) at the no. 1 kiosk. I snapped a picture of it to help me navigate the course.
Other Thoughts:
From the small parking lot, walk forward directly into the large field to get to the no. 1 tee near the kiosk bulletin board. You walk through a soccer field or along a gravel path to start. If 18 holes are not enough for you, there is an X hole (east of hole 11) and a Y hole (somewhat parallel to no. 18). Neither naturally flows with the rest of the course, but there you are if you are interested. I guess you would play X between 15 and 16, and you would play Y after playing 18 (walking back to near where you started for 18). I didn't always find the blue tee for some of the holes. There are three pads at no. 16, if I'm not mistaken. If you're not local to the area, I think pairing Sherando/Rockland/Jim Barnett makes for a good day trip with each course quite different from the other two.