Roger Sherman, a signer of the Declaration of Independence, was married twice. He married Elizabeth Hartwell, daughter of Deacon Joseph Hartwell of Stoughton, Massachusetts, in 1749. Twenty-six year old Roger was County Surveyor for New Haven County at the time so he took his new bride to live in New Milford, Connecticut. Elizabeth was known for her gentle nature and Christian character. That is about all that is known about her other than the fact that she had seven children before she died in 1760. The children were: John, William, Isaac, Chloe, Oliver, Chloe, and Elizabeth. The first Chloe and Oliver died in infancy.
Roger married Rebecca Prescott on May 12, 1763, when she was 20 and he was 42. Rebecca was born in Salem. Very little is known of her early life other than “she came from a long line of distinguished men and women and was a highly cultured and beautiful girl of great spirit” (Wives of the Signers – The women behind the Declaration of Independence, 94).
Roger and Rebecca met by chance one day when he had been to visit his brother Rev. Josiah Sherman of Woburn, Massachusetts. As Roger was leaving, Josiah decided to ride with him for a while towards New Haven. About the same time, Rebecca was traveling to visit her aunt – who was married to Josiah. The two brothers were about to separate when Rebecca’s “horse, with its fair rider, came galloping down the road. Aunt Rebecca was a great beauty and a fine horsewoman, and she must have ridden straight into Roger Sherman’s heart, for concluding to prolong his visit, he turned his horse and rode back with her” (Wives, 94-95).
Rebecca’s “beauty, grace, and wit were of the greatest help in” the career of Roger, a “wonderfully gifted but plain man” (Wives, 95). Rebecca was apparently very patriotic. When she heard that George Washington had designed a flag and asked Betsy Ross to sew it, Rebecca would not be satisfied until she visited Betsy to see the flag and actually sewed some of the stars onto it. Rebecca was later asked to make the first flag for the state of Connecticut. She was thirty-four years old when independence was declared.
Roger looked to Rebecca for her counsel in regard to business affairs as well as to public matters, and he relied heavily on her judgment. Roger and Rebecca were parents of eight children in addition to the five living children born to Roger and Elizabeth. Roger was gone from home most of the time doing business for the public, and Rebecca carried the responsibilities of home. She cared for her own children as well as those from Roger’s first marriage. Rebecca was held in high regard by all the children because of her ability and good judgment in handling her home responsibilities.