We started hiking it clockwise, in the winter, so when we got to deep snow, it became a out and back, not a loop for us. The only possible difference I can imagine is that the intersection of the trail and Tomboy Road is real obvious if you are on the trail. Going the other way, you *might* miss the left turn onto the trail and end up going up Tomboy.

I have only seen a few dogs on Jud Wiebe but the best hike for dogs would be the Bear Creek Trail. There's several areas where they can get wet crossing streams. The trail is wide and should be easy on their feet. Another short good trail for dogs is the Ridge Trail from St. Sophia station. We also like to take our dog on the trail that runs along Mountain Village Drive near the Golf Course. This trail is narrow and there's more runners so I would advise keeping your dog close. The River Trail in downtown Telluride is also nice, but full of people during the summer. Hope this helps!

Good question, don't know the answer, though.