I've been up this peak multiple times. It's a great day hike, usually there are few people the higher one goes, and the view is wonderful from the top. It's really nice seeing the lights below on the way up (or down) on summer evenings.
12 January, '16: 2nd of my traverse of S. Boulder Peak, Bear, & Green Mtn. Summited at 15.27. Wonderful views. Only one on the mountain :)
I've climbed Bear Peak many times in all seasons. I often run it for a great workout.