David Shepard was born in Westfield, Massachusetts, to John and Elizabeth Shepard, their eighth child of nine.
Yale college (1762–1769)
Shepard attended Yale at a time when the student body was caught up in the rebellious spirit of the 1760s. The students stopped going to classes and prayers and generally abused the tutors, who resigned. They would frequently speak against the British Parliament in chapel, and petitioned the Corporation with their grievances, insisting on the removal of the disciplinarian president Thomas Clap. Things at the college had become so difficult the Corporation ordered an early spring vacation, and David Shepard was one of the few undergraduates that returned. Despite the reduced student body, things continued this way until the end of the term. Commencements were usually celebrated with copious amounts of alcohol, despite the students resolving to drink no "foreign spiritous Liquors any more." The diary of one of Shepard's classmates records on September 9, 1766—the day before commencement—that they were examined for their degrees in the afternoon, but only after getting "Liquer in readiness for Commencement." Shepard graduated that September at what would be Yale president Thomas Clap's last commencement before resigning, Friday, September 10, 1766. The next year David married Margaret Clap, daughter of Ezra Clap on December 3, 1767. In 1769 David is included in a list of Master's degree candidates, his thesis relating to the nature of slow versus acute disease. This is the same year that his wife died, leaving him with one daughter, also named Margaret.
Murrayfield, Mass. (1770–1774)
He removed to Murrayfield, Massachusetts and married a second time to Lucinda Mather on January 7, 1773. They had six children: Mather, David, Lucinda, Harriet, Fanny and Horace. David Shepard was a Selectman of Murrayfield, serving throughout 1772-76, and for several years through the 1790s.
American Revolution (1775–1783)
As Boston's conflict with the royal government came to a head in 1773-75, Shepard was appointed to the Chester Committee of Correspondence. And at the battles of Lexington and Concord, April 19, 1775, he would serve as a volunteer surgeon. Following the Lexington Alarm, Shepard went to Cambridge as captain of a company of Minutemen in the regiment commanded by Col. Seth Pomeroy. On arrival, April 28, 1775, he was appointed Surgeon of Danielson's Regiment and remained at the fortifications in Roxbury, Mass. in that capacity through the remainder of that year. He later served with a detachment of the Third Hampshire County Regiment which marched to Ticonderoga to reinforce the army by order of General Schuyler, and was present at the Battle of Bennington, August 16, 1777.
United States Constitution
At a town meeting on December 13, 1787, Shepard was chosen as Chester's delegate to the State Convention to meet at Boston in January. And, in January 1788, Shepard was recorded at Boston, Massachusetts where he served as representative of the town of Chester at a Constitutional Convention to consider a constitution reported in the summer of 1787 by the Constitutional Convention in Philadelphia. On February 6 they formally ratified the U.S. Constitution, proceeding to the Boston State House for a reception. Shepard was reimbursed for his time and travel to a total of £14.14.0.
Amsterdam, N.Y. (1802–1818)
In 1802 Shepard purchased a farm near Amsterdam, N.Y., and resided there until his death. This farm later became the Fairview Cemetery.