I've done the Old Loggers Path three times now - I find it a great hike to be taking folks new to backpacking.
The direction you hike is really dependent on the mileage you want to do...I always hike it clockwise from Masten now. It's then about 11 miles the first day, about 11 the second day, leaving just 6 miles the third day.
Please feel free to PM me...I have a bunch of logs from my trips, photos, GPS data, etc. that I'm happy to share.
The trailguide that you can find online has you hiking the trail counter-clockwise. When I did it last May we had both campsites to ourselves, but there were lots of people going the other direction - one guy told me that there were more than 25 people at the site we had alone the second night! Just another reason for going clockwise...