Roger Sherman was born on April 19, 1721, in Newton, Massachusetts. Sherman's father William supported his family by pursuing farming and shoemaking. Sherman's mother, Mehetabel, was described as a woman of strong moral values who took great pride in instilling those values in her children. Sherman attended grammar school in Stoughton, where schooling was less than mediocre due to a lack of interest in and funding of education. However, Sherman was considered quite intelligent by the standards of his times due to his fascination with books and his relationship with Reverend Samuel Dunbar, the town's Harvard-educated pastor. Dunbar was said to have a strong passion in aiding motivated youth. With Dunbar's teachings and by reading numerous books from his father's library, Sherman became interested in such topics as theology, history, mathematics, law, and politics. In addition to spending much time reading, Sherman apprenticed his father to learn the art of shoe making. Sherman spent much of his younger years traveling to residences to fill the shoe repair needs of others. In June 1743, two years after the death of his father, Sherman moved to New Milford, Connecticut, to purse a more social and prosperous life.

Upon his move to New Milford, Sherman joined his elder brother, whereupon they opened the town's first mercantile. Sherman continued to work hard to make something out of his humble beginnings. Sherman's interest in his store took a back seat to his farming, shoe restorations, and his strong pursuit of mathematics. Because of this intense love and knowledge of mathematics, Sherman became surveyor of New Haven County while also obtaining officiating positions, such as being the town clerk. In 1749, Sherman married Elizabeth Hartwell, and they had seven children together, three of whom died in infancy. Elizabeth died in 1760, and Sherman married Rebecca Prescot. Prescot gave birth to eight children with Sherman, one of whom died in infancy.

Sherman was described as a man who enjoyed having his hand in many realms at once. He was a man who took on many duties and approached each one with vigor and full effort. During his time in New Milford, Sherman took it upon himself to prepare annual almanacs. During this time, almanacs took the place of newspapers in rural areas. It was said that besides the Bible, "no book held greater esteem." In 1750, Sherman published his first almanac. Information provided in these almanacs presented more than just material about sunrises and sunsets; Sherman also included poems, some of which he wrote himself, church notes, announcements, and proverbs. Sherman's almanacs were so highly regarded that on many occasions he was asked to contribute to The Ames Almanac, the most well-known almanac of the time. Sherman continued to publish almanacs for 11 years.

Because the colonies were in the beginning stages of development, there was no consistency in issues like currency from colony to colony. As a merchandise store owner, Sherman had to deal with deciding whether or not neighboring bills of credit should be used in Connecticut. In keeping with his strong desire to speak his opinion, in 1752 Sherman wrote a small inquiry discussing his feelings on such matters. In this inquiry, "A Caveat against Injustice," Sherman discussed the consequences of fluctuating mediums of change. He believed that the disparity between Rhode Island and New Hampshire's bills of credit forced down the value of Connecticut's. He suggested to the Connecticut General Assembly that prevention of the circulation of Rhode Island's money be administered in Connecticut.

In continuing years, Sherman became very interested in law. In 1754, he was admitted to the Bar as an attorney in Litchfield, where he continued to show great competence. In May 1755, he was appointed justice for Litchfield County, while at the same time elected to the General Assembly of Connecticut. Four years after being admitted to the bar, Sherman became justice of the Superior Court of Connecticut. By 1761, Sherman grew tired of practicing law and decided to move to New Haven, Connecticut, where he opened a store across from the Yale University campus. He then became highly involved with the university's efforts for many years. In 1765, he was elected Yale University Treasurer, a position he served for 11 years. In 1768, he was awarded an honorary M.A. in token of his great dedication to the university's progress.

In keeping with his drive to constantly become involved in new efforts, Sherman wholeheartedly threw all he had into political matters. In 1773, he was elected to the first Continental Congress. Sherman hoped to create colonies that would create their own laws so they would not have to be under Britain's strong influence. While holding this position, Sherman was influential in providing ideas that would help begin many of the United States' important foundations. In 1774, Sherman served on the committee that helped draft the Articles of Association. Sherman was very vocal and spoke often during his Continental Congress meetings. He was described as awkward in his presentation, yet always provided "sound judgment and a clear head."

Sherman is best recognized as one of the founding fathers who helped draft and sign the Declaration of Independence. During the Constitutional Convention, Sherman was noted as one of the most frequent speakers. He is credited with delivering 138 speeches regarding the Declaration. He focused his efforts on defending the importance of the smaller states, such as his home state of Connecticut. Initially responses to his arguments were only well taken by other smaller state representatives. The day after his appointment to the Declaration of Independence drafting committee, Sherman was appointed to help draft the Articles of Confederation. While serving in the Continental Congress, Sherman was assigned to many committees dealing with issues like foreign affairs and finances. It is said that Sherman laid the foundations for our current-day Treasury Department.

In addition, Sherman is noted as a main mover of the Connecticut Compromise. The Compromise proposed that each state have one house vote regardless of the state's population or size. The Connecticut Compromise combined with the Virginia Plan and New Jersey Plan to create what is known as The Great Compromise. Sherman is also credited with the foundations for the New Jersey Plan, which discussed the pertinence of each state being equal in their representation in Congress.

Sherman can also be acknowledged for developing the U.S. Constitution. In addition to signing it, Sherman is credited with providing 11 features of the Constitution. Sherman then went on to present his support for ratification of the Constitution by preparing his fellow residents of Connecticut with a sequence of five letters in the New Haven Gazette. These letters, called "To the People of Connecticut from A Countryman," discussed the importance of ratifying the Constitution.

During his later years, he engrossed himself in the teachings of theology. He is credited with writing several small sermons on religious matters. One of the most well-known is titled "A Short Sermon on the Duty of Self-Examination: Preparatory to Receive the Lord's Supper," and it discussed the importance of self examination during communion and goes on to cite the importance of acknowledging one's love for God.

In 1789, he was elected to the First Congress and served until March of 1791. During his time in the Senate, Sherman was appointed as one of only 11 members to prepare the rules and orders for Senate procedures. Sherman served in the Senate from March 1791 until his death from typhoid fever on July 23, 1793. Sherman was laid to rest at Grove Street Cemetery in New Haven, Connecticut, located close to the Yale campus. Roger Sherman's efforts toward the creation of the United States were substantial. He is recognized as being the only member of the Continental Congress to have signed the Articles of Association, the Declaration of Independence, the Articles of Confederation, and the Federal Constitution. In honor of Roger Sherman's contribution to the United States Constitution, a main street in downtown Madison, Wisconsin, is named Sherman Avenue.