ORLAND EARLY SETTLERS PENNY JO AMES
The earliest settler in Orland, Then Plantation 2, was Joseph Gross, who came fro Fort Pawnal, now Fort Point, in 1764, and settled on the lot now occupied by T. O. Sanders on the Castine Road, according to information contained in the Orland Census Report 1907.
A brother Ebenezer Gross was the next settler, He came from Boston to Gross Point in 1765. Samuel Craige settled just below Joseph Gross in 1766, He bought of Dr, John Herbert, who was employed as a schoolmaster in 1775. Joseph Viles came from Milton Mass.., in 1767 and settled where the Harriman family still lives in (2000) on the Castine Road, Mr. Viles built the first framed house in No. 2 in 1777,
Zachariah Gross, son of Joseph, was the first white made child born in Orland in 1766, The first death in the Plantation was that of Samuel Cushing who was drowned in Eastern River May 17, 1770, and was the first buried in the "old Burying Ground" (his slate stone is visible today).
Between 1768 and 1780 quite a number of settlers came from Boston and vicinity and took up lots on the east side of Eastern River. Among the most noted were John Hancock, Samuel Keyes, Samuel Soper, Calvin Turner, Asa Turner and Humphrey Holt.