Hi all, I'm in the beginning stages of planning a Long Trail hike late this summer/September (in hopes of vaccines working and resupply & shuttles being easier), and it occurred to me, why don't I just walk the rest of the way? I'm in the Pioneer Valley of Massachusetts so basically I'm looking at how I might hike between the southern terminus/Williamstown and Greenfield or Amherst. Haven't firmly decided NOBO or SOBO yet. If I do this bootleg thing, I'll probably go NOBO to get the hard/janky part done first.

The state forest and their trails cover a decent chunk of mileage, and my All Trails research last night shows a ton of other trails, but I suspect they're not much, not blazed, and perhaps non-existent. Obviously I don't want to walk 30+ miles on a highway, but it's some beautiful country between the AT and the Connecticut River, just a lot of up & over. Even back roads between forests/conservation land would be beautiful, but I'd like to string together as much non-motorized mileage as possible, obviously.

Has anyone here done this kind of bootleg planning before? I do realize depending on my timing, we're getting into hunting season, and I'm well practiced at stealth camping. I've got time to go check out stretches of trail to confirm travelability, but things could be quite overgrown between now (or even May) and August/September.

My sense is that All Trails is unreliable at best for anything that isn't an actual user-reviewed trail. Where does All Trails draw that data from, anyway? Any suggestions for finding the little trails that generally only locals know about that are all over New England?