Hi Sean,
I have played Whitinsville 4 times (played nine 4 times), all practice and tournament rounds in preparation for a Massachusetts Golf Association amateur qualifier.
Eight and Nine are definately the most intriguing holes on the property.
Eight is a shortish par 4 of about 320, and the tee shot is challenging. The shot angles over a marsh area to a fairway that jogs hard left towards the green. One can aim much further left than it appears from the tee, but that line is over the most marsh, and a bunker. I do not remember the green being that interesting, but it was a while ago I was there.
Nine is one of Ben Crenshaw's favorite par fours. The hole is about 435, doglegging right. The hole goes straight for rougly 270 yards before plunging down into a gully. Anything right off the tee will find a long slope or the pond at the bottom. The green is elevated with fairway running up to it from the left, generally flat and the same elevation as the first fairway on the other side of the dip. Bunkers flank the green left and right, but the front is open. The biggest challenge is which club to hit off the tee, and where to place the drive. Many Ross courses around the Boston area have long par fours designed with the natural terrain to force the player to club down off the tee (often a fairway wood), and force a long iron to the green. Long hitters can blast through the fairway on these holes and usually be ok (like at #9 at Whitinsville), but their 8-9-PW approach will be hit from thick rough and an uneven lie. It's sort of the 1920s-1940s version of the PGA tour debate on whether to hit driver on every hole to be closer to the green irrespective of lie in the fairway or rough.
As for other holes at Whitinsville, #1 has a fun push-up green to the reachable par 5, #2 is a cute short semi-blind par 3 surrounded by bunkers and rough, #s 3-4 go across a local street and are medium-length par fours, one uphill, one severely downhill. #3 sports a sort of split fairway, higher on the right gets a better look at the elevated green. You can see some great Ross rock-pile mounds in between these two holes, and some behind the green on #4. #5 is a blind-drive long par 4 that plays downhill, the drive framed by fairway bunker not really in play these days. #6 is a lazy dogleg right to a green in a very wide-open area, much like the rest of the 9 on the clubhouse side of the street. #7 is a medium to longish par 3 out in the open, exposed to the wind.
It is a wonderful course, truly one of the best classic (if not just best) 9s in the US, but alas, it only has 9.
-Brad