Dolley’s next step along her great adventure began in January 1790 when she married John Todd, a Quaker lawyer in Philadelphia. Their courtship was quick with a wedding and two sons, John and William following close behind. When her mother left Philadelphia in 1793, Dolley's sister, Anna Payne moved in with the Todd’s to help with the children. In August 1793, a yellow fever epidemic broke out in Philadelphia killing more than 4,000 people over the spring and summer months. Sadly, by mid-September, thousands had fled the city except for Dolley. She stayed behind to care for her husband, John and son, William. Unfortunately, they contracted the virus and sadly died soon after of yellow fever within hours of one another. She was a widow by the age of 25, with her young son John to support. At this point, Philadelphia had just become the capital city. It wasn’t long before Dolley caught the attention of many men, including James Madison, who was 17 years her senior. Her charm combined with the most striking blue eyes, fair skin, and black curls, not to mention her pure desire to please was an instant attention grabber. James Madison didn’t waste any time, even though they had a few differences in background, they were married within months of meeting on September 15, 1794. Dolly was so in love with James she even relinquished her religious identity to marry him since he wasn’t a Quaker.
For the next three years they remained in Philadelphia. However, by 1797 Madison decided it was time to retire from politics after eight years of serving in the House of Representatives. He packed up his family and returned to his plantation in Montpelier, Virginia. By 1800, his passion was reignited when Thomas Jefferson was elected as the third president of the United States, selecting Madison to serve as his right hand man and secretary of state. Dolley Madison made her presence known in Washington from the moment of her arrival. Since Thomas Jefferson was a widower, he regularly called upon the elegant and vivacious Dolley to serve as his first lady at official functions. Furthermore, she was chief contributor to the development and decoration of the White House. With Dolley by his side, in 1808, the Democratic-Republican caucus nominated James Madison to succeed Jefferson. Madison won two terms in office, serving from 1809 through 1817. In 1817, James Madison retired from politics for good. He and Dolley returned to their Montpelier plantation in Virginia where they remained until James Madison’s death on June 28, 1836. Dolley’s financial situation took a turn for the worse due to the exploits of her son, John. In 1830, John went to debtors’ prison in Philadelphia causing Dolley to sell land and even mortgage half of the Montpelier plantation in order to pay his debts. The year following James Madison’s death, Dolley organized and copied her husband’s papers. Congress generously authorized $55,000 as payment for her work in editing and publishing seven volumes of those collected papers. By mid fall of 1837, close to a year after her husband’s death, Dolley decided to return to Washington, moving into a house on Lafayette Square. She hesitantly left John in charge of the remaining portion of Montpelier; however it quickly became evident that his alcoholism rendered him incapable of maintaining the plantation properly. In attempt to support her and John, she tried to sell the second half of James Madison’s papers, but when unable to find a buyer sold the remainder of Montpelier plantation and its slaves. Dolley Madison died peacefully at her home in Washington on July 12, 1849 at the age of 81. She was initially buried at the Congressional Cemetery, however she was later was re-interred at Montpelier, where she now rests next to her husband.