Bear Mountain Number 2
This one is very near the Overlook Lodge, which I believe is the alternative lodging for the area if you're not staying at the Bear Mountain Inn. In fact, the Overlook Lodge is where I parked before climbing down the steep slope to the cache.
Bear Mountain Number 3
This one is a lot closer to Route 9W so that's where I came in from. The trails in this area were very muddy and wet (with flowing water) but were still walkable. I must be better at going uphill now as this morning's walk up is not even close to being as difficult as I remember. The colder weather probably helps a lot too.
This is just down the trail about 0.6 mile from Bear Mountain No. 3 so I went for it too. It's in Doodletown, or to be more specific, at the former site of a school building. It's a ghost town. Several cemeteries remain but not much of the foundations. Nothing remains of the school although a sign marks the location.