Both titleholders are extremely accomplished, Kelly is a Harvard graduate and is currently attending the Harvard Business School to complete an MBA. Annie just started at Harvard and is there studying government. Their bios are on their profiles (click the links above) and are well worth reading, because there's more to their stories than just that snippet.
Kelly was third runner-up in last year's pageant, and is the seventh consecutive titleholder who had made the top five in either a Miss USA or Teen USA pageant. Annie competed in her home state of California last year (she is from the Bay Area) and made the top 20.
The top 16 included previous New Hampshire and Rhode Island runners-up Nina Murray and Nicole Eacuello, past semi-finalists Fatima Armaghan, Meghan McInnis and Rachel Miller, past non-finalists Ashley Maiolatesi - from Louisiana last year - and Alexandria McBride - in Illinois in 2017, and newcomers Jaclyn Delmonico, Shumika Jean-Baptiste, Adriana Taylor and Shelby Thiem.
Miss Massachusetts Outstanding Teen 2017 Carly Fisher made the top 16 in her first attempt at Miss MA Teen USA; others in the top 16 were 2018 semi-finalist Kiersten Khoury, 2018 Washington teen semi-finalist Marianne Baptista, and newcomers Kennedy Campbell, Yara Fawaz, Jasmine Hachem, Jacey Hinton, Dalia Karim, Gianna Puopolo, Alexis Renaud and Eliza Rossi.
See also: Miss Massachusetts USA & Teen USA state pageant results | Miss Massachusetts USA & Teen USA titleholder history
1RU: Ashley Baptista (1RU 18, 2RU 16, SF 15)
2RU: Chelsea Demby (2RU 18)
3RU: Sabrina Victor
4RU: Isabelle Varga (2RU NJ TUSA 16, SF 15, SF 14, NF 13)
Fatima Armaghan (SF 18)
Nicole Eacuello (SF 18, SF 16, 3RU RI USA 15, NF 14, NF 11)
Ashley Maiolatesi (NF LA USA 18)
Meghan McInnis (SF 18, NF 17)
Rachel Miller (SF 18)
Nina Murray (SF NH USA 18, 2RU 17, NF MA TUSA 14, NF 13)
Alexandria McBride (NF IL USA 17)
1RU: Juliana Mazo
2RU: Noor Mohamed
3RU: Olivia Lindberg (SF 18)
4RU: Emily Pimentel
Marianne Bautista (SF WA TUSA 18)
Carly Fisher (MA's OT 17)
Kiersten Khoury (SF 18)