Her maternal grandmother immigrated to the United States from northern Italy after World War I, and her paternal grandfather was a Plymouth, Massachusetts native with roots in Ireland as well as on the Mayflower.

Swift attended North Adams public schools, and in 1987 graduated from Trinity College in Hartford, Connecticut, with a degree in American studies.

[6] She was instrumental in the passage of the Education Reform Act of 1993,[7] which created the Massachusetts Comprehensive Assessment System, one of the nation's first statewide programs for quantifying academic performance.

"[3] It was in this capacity that she developed political themes of increased accountability, smaller government, fiscal responsibility, and reforming education and social services.

[9] In 1996, rather than seek re-election to the Senate, Swift was the Republican nominee for United States Congress in Massachusetts's 1st congressional district.

[10] She was especially criticized for using staff members to watch her daughter, and for her Massachusetts State Police detail's use of a helicopter to avoid Thanksgiving traffic en route to her home in The Berkshires when her baby was sick.

In an ethics ruling that Swift herself requested, she was found to be in violation of state guidelines for the babysitting and she paid a fine of $1250, but she was cleared of wrongdoing on the question of the use of the helicopter and on allegations that staffers helped her move from one Boston-area apartment to another.

[11] Twenty years later, Boston reporter Joanna Weiss reflected on the gender bias that faced Swift throughout her tenure.

She made national headlines when she continued to exercise executive authority during her maternity leave, including chairing a meeting of the Massachusetts Governor's Council by teleconference while on bed rest for preterm labor.

"[14] After it was learned that some hijackers boarded planes at Logan International Airport in Boston, Swift came under political pressure and forced the CEO of Massport to resign.

In February 2002, she drew criticism for her refusal to commute the thirty-to-forty-year sentence of Gerald Amirault, who was convicted in the 1986 Fells Acres day care sexual abuse trial and who had already served 16 years in prison.

[21][24][25] Many Republicans viewed her as unable to win a general election against a Democrat and campaigned to persuade businessman Mitt Romney to run for governor.

[35] Swift and her husband owned and operated Cobble Hill Farm, a horse boarding facility and riding school in Williamstown, Massachusetts, where they lived with their three daughters before relocating to Vermont.

in Math from the University of Massachusetts, Amherst, while her other two daughters, Lauren and Sarah, graduated from Burr & Burton Academy in Manchester, Vermont, in 2019.