It depends on what you want to sail it in. If you have a sailing
kayak, you can do it easily. Your
Ericson could not do the trip for a number of reasons including the ones mentioned above. The trip is much more enjoyable going downstream though, there is a decent amount of
current. All of the dams/rapid are portageable. The long ones have a shuttle
service that is provided and the short ones, you do yourself.
I have paddled the Connecticut from northern NH to LI sound in a canoe and we actually sailed a good portion of it. It is a great trip but it isn't really a sailing trip, it is more of a canoe/kayak camping trip.