Heading down to the Northampton area (staying in Hadley) this weekend through Monday for a quickie vacation meetup with another couple. Bringing the tandem plus two, or three or four if I can think of a reason, single bikes -- our friends, who live in a small apartment in NYC, don't currently own bikes. All four of us are decently athletic, but I'm the only one who will regularly bike 50+ miles in a day.
Planning to do the Manhan and Norwattuck rail trails and enjoy the new connecting bridge. Other ideas? I've stayed for a couple weeks at a time in the past, and commuted a lot from South Hadley to Northampton -- but some of those hills are probably too hard for my companions.
Any dirty-but-easy trails? In addition to the tandem, which I'm not comfy taking on anything rougher than flat dirt roads, two of the single bikes I bring will likely be my and my wife's (brand new-to-her surprise) hardtail mountain bikes, and if I bring the other two single bikes, they'd be our rigid cross bikes which I can stick 42mm knobbies on.