I'm not much for point-to-point anything in the outdoors. These kinds of trips require a dedication to planning and logistics that, thanks to my undiagnosed hyper-thyroid and ADHD, I just don't have the time or patience for. This attitude excludes me from a number of fine outdoor sports that others seem to thoroughly enjoy. Sea kayaking (barf), canoeing (great when done from a dock with a beer in hand), pub crawling (inherent danger of never knowing where you might end up, or with whom), and most of all long distance hiking.
Point-to-point sporting enthusiasts have put a lot of work into the trails they've created, and there's no shortage of epic treks to be had here in New England. Vermont's has it's own version of the Appalachian Trail in the 272 mile Long Trail. For epic paddles you can float the Roger's Rangers route up the Richelieu from Lake Champlain to the St. Laurence River. Epic road riding? There's the Harpoon Point-to-Point, or, for the truly insane, the 1200 km Boston-Montreal-Boston Randonee. And with plenty of great through-routes in the Whites, it's not exactly slim pickings for skiers either.
Mountain bikers, on the other hand, have a long day at Kingdom Trails and... the Catamount Trail?