Have you been to
Bash-Bish Falls? At Mt Everett State Forest you can drive up to a parking lot (on the map, it's right by the pond) with easy trails around the pond plus picnicing, and it's not hard at all to hike up to the (now-closed) upper parking lot and then from there to the summit.
That whole South Taconic area is full of open ledges and views despite not being that tall.