Ran this FKT self-supported as part of a 100km run from home.
I ran the loop CW starting at gate 8-2. I think CCW is a little faster, as the downhills are more gradual and runnable. Either way, I always like to get the most technical miles on the NET along 202 out of the way in the first half.
Ahead of time I had dropped bottles and gels at gate 10, gate 27 and the visitor center. As such I carried 3 bottles and 6 gels at most, 2 bottles in my belt, and 1 hand-held (from gate 27 - for that 32 mile stretch). There is also several options to drop bottles on the east side, I just didn't want to drive the whole loop ahead of the run. The belt got pretty bulky with the two 16oz soft flasks, 6 gels and phone, still like a belt over a vest/pack. In the winter only the port-a-potties at the 2 dams and the tower were available, in the summer there's more available on the north side and east side.
The trails were fairly wet and slow, but not icy or slippery. The Quabbin trails were not bad at all, but I couldn't keep my feet dry on the NET section, which also featured a challenging creek crossing.
Overall, I just love this route, winter or summer. More people should come out and try it out.