“Orlando Ware was born in Sherburne, Mass., the twenty-ninth day of August, 1779.  His father, John Ware, was a brother of Henry Ware, senior, late Professor of Divinity in Harvard University, and his mother was daughter of Caleb Leland, and granddaughter of Ebenezer, who was son of Ebenzer and grandson of Henry.

He was for many years concerned in business as a merchant in Deerfield, Massachusetts.  But for a few years past he has been engaged in farming.  And he is what may be properly called a Gentleman-Farmer.  He has been called upon for many years by his fellow citizens in Deerfield, to fill the more important municipal offices in the town, and has held the office of selectman and overseer of the poor, for the period of twelve years.  He represented the town in the general court for the year 1819, and again in the year 1840.”

Source:  The Leland Magazine: or A Genealogical Record of Henry Leland, and his Descendants, by Sherman Leland, Printed by Weir and White, Boston, 1850, page 25

“Orlando Ware lived in a house at the corner of Memorial Street and Deerfield’s main street, but he kept a general store on the common from 1802 to 1831. With few exceptions, the Orlando Ware account books are complete from 1803 to 1830. In addition to his role as storekeeper, Ware served as selectman for ten years as well as filling other town offices. He married Deborah Starr (1780-1846) and they had ten children, five of whom lived to adulthood. In 1841 he sold a building lot to his son Edwin at the south end of his homelot; Edwin Ware built a house there in 1842 in the Greek Revival style.”

Source:  Memorial Hall Museum