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- Simeon Tupper Sr. was born in 1729 in Stoughton Massachusetts (15 miles SW of Hingham). He had seven brothers (Mayhew, Seth, Reuben, Judah (died as baby), Levi, Judah, and Benjamin) and one sister (Joanna).
Simeon Tupper Sr. married a lovely young lady from Dorchester Massachusetts named Anne Capen. Simeon Sr. was a cordwainer by trade. A cordwainer (or cordovan) is somebody who makes shoes and other articles from fine soft leather. The word is derived from "cordwain", or "cordovan", the leather produced in Cordoba, Spain. Historically, there was a distinction between a cordwainer, who made shoes, and a cobbler, who repaired them.
Simeon and Anne had four sons ( Simeon Tupper Jr., Thomas, Ebenezer, and John) and four daughters (Elizabeth, Hannah Susan and Lois). In 1762 the family moved to Pittsfield Vermont. Simeon Jr. was born in 1765. In January 20, 1777 Thomas Tupper joined the Continental Army mustering in the town of Ashuelot Equivalent. He was recruited by Truman Wheeler, who was the Muster Master for the county. He entered the army as a private under Colonel John Bailey's 2nd Massachusetts regiment. He enlisted for two years. His company camped at Valley Forge in the winter of 1777/1778. The army was poorly supplied and ill equipped for the winter. They suffered hardship and many did not survive the winter. He died serving his country in battle at the age of 24.
Simeon Tupper Sr. had enlisted early in the war, on August 4, 1775, and his first mission was to March from Pittsfield to Canada. The regiment was dismissed on December 30, 1775 after 22 weeks and 2 days of service. Just before Thomas' death, Simeon Tupper Sr re-enlisted along with his son Simeon Jr., joining the Continental Army in 1781. Simeon Sr was 51 years old and Simeon Jr. was 16 years old. Simeon Jr. was only 5' 3" when he enlisted. They joined in early 1781 both for a three year enlistment. They were assigned to a regiment commanded by Colonel Benjamin Tupper (Simeon Srs. brother). Benjamin was in the army for six years, and the most noteworthy events for his regiment were Ticonderoga and Valley Forge. The conflict ended in 1783 and the Tuppers returned to their home in Pittsfield Vermont.
Source: Massachusetts Soldiers and Sailors in the War of the Revolution Volume 16, pages 148-149
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