There’s scant information regarding any major villages within the Bearpen Mountain vicinity although it probably was used as a hunting location by the Delaware Indians who populated the region. Most of the Native Inhabitants made camp near the Delaware River and the East Branch and probably used the interior of the dense and mountainous forests as a way to travel to other regions while settling in more habitable locations.
Anyone familiar with the area could understand why although I usually question as to the reason pioneers settled in the desolate mountains and hollows that populate the Catskill Region. It was a hardscrabble way of life to eke out an existence among the bear, mountain lions and wolf packs that were prevalent. Take into consideration that the hard clay soil didn’t encourage nor support farming.
The Delaware Indians are referred to as Tuscarora, Lenape, Mohawk, Esopus, Mohicans although most early references to the first inhabitants simply identify them as ‘Indians.’
Some interesting reading on Delaware County is linked here: