@AlexH-C and @REI-JenK I have tons of ideas in the Whites. No knowledge of that part of Massachusetts though. If you want to go into NH I can suggest a few trips. Near you Alex is Mt Cube, part of the AT and east of Hanover NH. Either North or South peak would be great. Another less well known Mt with a sweet trail is Paugus. Approach via Cabin Trail for a gentle 9 mi round trip hike. There are several spots up top all mossy and ready for a tent.  Not part of the AT but it is further from you: east of Lincoln NH off the Kanc. But what a nice drive!