Nice write-up. I did that ride last year, including the trail, with a fellow iBOB--took the train down and met at the GWB. Brought back lots of memories, though I could not convince him to do the first section via River Road (and some of 9W is kinda nasty, with shoulders in poor condition--ask around, there are alternate routes, safer and more scenic.)
Back in the day that was the long day training ride, from NYC to Bear Mt. and back You had the basic Muffin Ride, to Nyack and the Runcible Spoon and back, about 50 miles, then Rockland lake, about 75, and the Bear being the full monty. The Century Road Club had a tradition back then of riding out and back on New Year's Day, with something like a lap and a half of Central Park completing the century, IIRC. It was the first, highly unofficial race of the season. I think someone was at the Lodge so you could sign in. I always started my season training January 2nd, and so had to miss the fun.
These days for me it's a straight shot down 9D from Beacon, with the return on the other side of the river, usually up Storm King via 218, maybe cutting through West Point, then back over the Newburgh Beacon bridge.