The earliest settler in Orland, then Plantation #2, was Joseph Gross, who came from Fort Pownal, now Fort Point, in 1764, and settled on the lot on the Castine Road. A brother, Ebenezer Gross, was the next settler; he came from Boston, Mass., 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 school master in 1775. Joseph Viles came from Milton, Mass., in 1767. Mr. Viles built the first framed house in No. 2, in 1777. Zachariah Gross, son of Joseph, was the first white male child born in Orland, born in 1766. The first death in the Plantation was that of Samuel Cushing, who was drowned in Eastern River May 17, 1770 and was buried in the “Old Burying Ground”.

Between 1767 & 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 of these were John Hancock, Samuel Keyes, Samuel Soper, Calvin Turner, Asa Turner and Humphrey Holt. In 1781, Ezekiel, Peter and Asa Harriman moved from Plantation No. 1, (Bucksport) and took up settlers’ lots here. Jas. Ginn came from Brewer and succeeded Robert Treat at the mill until 1797. In the mean time he built one Brig and two Schooners. In the latter year he moved to Bucksport and Mr. Treat sold the mill and lot to John Lee of Castine, who did a large business. About 1816, Joseph Lee succeeded his uncle.

In 1773, Michael Davis, and old hunter, came from Concord, Mass., and took up a lot on a ridge of land three miles from any settlers. He lived a solitary life until James Smith, Nathan Hancock, John Gross, Joshua Gross and Andrew Craige took up settlers’ lots near him, which were run out in 1780. Except Jas. Smith, these where sons of the first settlers in the plantation. In 1791, Jacob Sherburne removed from Hampton, NH and took up a lot at “Sherburne’s Point“. In 1784, a petition sent the General Court complaining of the laxity of the original proprietors was signed by fifteen settlers. One of these Samuel Craige, Jr. erected a frame house on the “Falls Road”, which was said to be the oldest house in town. Jonathan Gilpatrick was the first blacksmith; his shop stood on the site of the former Universalist Church. Eliakim Darling, an old time schoolmaster, settled on Gross Point but later moved to Bucksport. Simon Gross, John Gross, Wm. McIntyre, John Partridge and his sons, Daniel, Thomas and David; and Wm. Moses and Edward Sanders where here before 1800. Barzilla Hopkins removed from Orrington to Leach’s Point. Richard Patch settled at the outlet of Heart Pond. In 1799 there were 70 polls assessed in the Plantation. Real estate was valued at $24,110.96 and personal property at $15,026.05.

The next year, 1800, the town was incorporated.