Great question — answering as the UphillTech team:
There isn't a lot of wilderness near Boston, but there are many local trails. Camping is not allowed on most land that local trails pass over. However, it is sometimes possible to get permission. It is probably possible to string together a loop on local trails with pre-arranged camping permission in specific areas. You would have to do a lot of digging to find the many local trails, find a decent sized loop, then look for camping permission at a few selected sites along that loop. If you are willing to spot a car instead of requiring a loop, then you have many more options. There are more regional trails in the area than most people realize. These are long enough for 3 days of hiking. The...
Full answer by Olin Lathrop: https://outdoors.stackexchange.com/a/17410 (CC BY-SA 3.0).
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