I ran this route on September, 12th 2015 in 4:31:32, unsupported. Strava data HERE. I started at Ledges Trail and ran counter clockwise. I know of no other attempts at this, but I also don't know where to look for these things besides this site. If anyone has run this route, or knows of someone who has, please post an update. Or, if you think there is a cooler variation that people should be doing instead, happy to hear about it. Pleasant Mountain has some great trails and is not a far drive from Portland and southern New England. This route still has plenty of room for faster times.
4h 31m 32s