Breakneck Ridge is probably the most famous NYC-area hike, and I've done it once before. It's always crowded (in some cases with people who have no business being there), but it's still worth it for the spectacular views of the Hudson River and Storm King.
Most people turn around and go back by an alternate trail once they reach the top, but we left the crowds behind and continued on to Sunset Point. It wasn't sunset, and it wasn't quite as amazing as the name would suggest. Actually, we had a lot more amazing views on the way, what with all the leaves being off the trees, like this one:
From there we kept on to the South Beacon Fire Tower. This photo looks north from the tower toward the Beacon Reservoir. The tower itself is 62 feet high and was only restored a couple of years ago. The crowds picked up here, since you can also get to the tower from several other directions.
We took the Wilkinson Memorial Trail back to Sugarloaf Mountain. Along the way, we encountered three jacked-up jeeps driving on the trails. This is your reminder that (a) this is illegal and (b) there are a lot of hikers on these trails, so this is an accident waiting to happen. Accept the fact that you can't take your preferred mode of transit everywhere (whether it be horse, bike, car, or even your own two feet) and don't be a jerk.
We reached Sugarloaf at Sunset, hoping to see the Constellation installation on Bannerman's Island. While we could see it, it didn't look like much from that angle; word on the trail is that the best way to see it is by kayak. From there, it was headlamps on, down to the train.
Our leader estimated the hike was 14 miles, and my watch gave our cumulative altitude as 4,200. I don't know if that's accurate: Up Breakneck is 1,250, and we had at least two more significant ascents, but that still may be high.
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