Hi Jon,
Your PM box is full. I've been out of town for a week or so. Around here (NY state), public riding is extremely limited. To get serious mileage and varying terrain of the type you are talking about, we attend Turkey runs. My advice would be to plan your trip around a one of the NETRA Turkey runs. These are great non-competitive organized rides with plenty of "Hero" sections for those that want them. You'll meet a lot of riders there too. They are typically in VT, NH, MA, or CT and will run about 70 - 100 ground miles. The "Ammo" run in NH and the Berkshire Triple B both have their share of mountain terrain.
http://www.netra.org/Schedules/scheduletr.htm
You'll have to join NETRA and AMA (about $35 each) but you can do that at the event. No club can get event insurance without the AMA anymore, hence the membership requirement. Think of it as a vacation expense. Also, if you join NETRA in advance, you can order trail maps
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http://www.netra.org/store/information.htm#Where to Ride>
Also, try posting in the "Places to Ride" forum, others may have info about MASS & NH riding that I don't.