The first inhabitants of the area were the Fork Indians of the Delaware Nation. They made their headquarters at a place on the south slope of Buck  Mountain in the general direction of Nescopeck on the Susquehanna River and began making repeated attacks on settlements in that area. The first  white settlers to see Freeland were a detachment of the colonial militia in the fall of 1780 under the command of Captain Klader. Klader's mission was to meet Colonel Hunter of Northumberland County in an attack on the Indians.

Captain Klader and his company left Stroudsburg and crossed the mountains to the Lehigh River which they forded near the present site of the village of Rockport. From there they followed the old Indian trail that led up over Buck Mountain and across the top of the hill to the southeast of where Freeland now stands. They descended on a trail into the Conygham Valley and stopped to rest when they were ambushed by the Indians. A few men survived the attack but the first white man to set foot in the Freeland area died without being able to tell what they had seen. Captain Klader and the majority of his detachment is now buried about a half mile from the town of Conygham.