Kbomb, good job on this trail. It's one of my favorites, and IMO you were wise to go clockwise your first time on it, as it's harder to follow counterclockwise in my experience.
The Whiskey Jack site is one of the nicest, most secluded sites in the BWCA but there have ben pieces written about it in Backpacker and other national magazines so it's often taken on summer weekends; best not to plan on it being available, and to keep enough energy in reserve to hike the extra two miles either direction to the next site.
Dolpho, this is a well used trail by BWCA standards but it can still be fairly hard to follow when the leaves are off the trees, and a coating of snow would make it trickier still. As noted above I think it would be easier to follow clockwise, and your only challenging spots would be on the east side. Only you know if your navigation skills are solid enough, of course.
I'm not a terribly experienced winter hiker so I don't know how confidently I can answer that question. I'd guess that most of it would be doable, with the most challenging part being the NE stretch of trail where it crosses over a couple portages and over a few big granite fields that made the trail a little difficult to follow were it not for the cairns.
Nice report Kbomb. I have wanted to hike this loop for many years but still haven’t gotten there. How visible and navigable to you think this would be with a few inches of snow cover? I would only have map and compass without a gps track file to follow and not in the mood for wandering off trail.
New Trip Report posted by kbomb
Trip Name: Angleworm Solo Backpacking.
Entry Point: 20
Click Here to View Trip Report