I've had an impractical ADK through trip rattling in my head for many, many years. The relatively recent NYS acquisitions of the Essex Chain Lakes makes the trip possible, but no more practical...Unless, a pair (or more) of paddlers were to start at opposite ends of the trip, passing along car keys at some midway point, to ease the car shuttle.
Here's one version: Rock Lake to some of the Rock River, a bit of a bushwhack to avoid the non navigable sections, rejoining the Rock at the confluence with Dun Brook. Down the Rock to the Chain Drain, up the Chain Drain and thence through the Chain Lakes and out. Sections of the Rock require carries, there are no trails, no paths. Of course, the other paddler (or group) starts from the Chain Lakes.
Not necessarily all that long, but parts of the Rock are very rarely paddled.
There's another version including the Cedar River, the Rock, and the Chain Lakes, but a good portion of the Cedar would be quite challenging for the upstream paddling person (or group).