The Miss Massachusetts USA competition is the pageant that selects the representative for the state of Massachusetts in the Miss USA pageant. It is currently produced by The Clemente Organization based in Malden, Massachusetts, which also produces the Maine pageant.
Shawnae Jebbia was crowned Miss USA in 1998 and Susie Castillo won the crown in 2003. Both Miss USA winners from Massachusetts were asked the same final question during the live telecasts. The most recent placement was Melissa Sapini in 2024, placing Top 10.
Kayshauna Montaño of West Springfield was crowned Miss Massachusetts USA 2026 on June 21, 2026 at DoubleTree by Hilton Hotel Boston North Shore in Danvers. She will represent Massachusetts at the Miss USA 2026 pageant.
Gallery of titleholders
Results summary Miss USAs: Shawnae Jebbia (1998), Susie Castillo (2003) 1st runner-up: Diane Pollard (1978) Top 10/12: Monica Magnus (1979), Janet Marie Flaherty (1982), Mercedes Waggoner (1985), Kristen Mastroianni (1995), Jacqueline Bruno (2008), Melissa Sapini (2024) Top 15: Sandra Ramsey (1957), Barbara Feldman (1960), Elaine Cusick (1961), Sandra Smith (1963), Nancy Brackett (1966), Sarah Kidd (2013), Allissa Latham (2018) Massachusetts holds a record of 16 placements at Miss USA.
Awards Miss Photogenic: Annika Sharma (2023), Melissa Sapini (2024) Miss Congeniality: Stacey Blaine (1993) Best State Costume: JoAnne Savery (1981)
Winners
Color key
Year Name HometownAge1 Local title Placement at Miss USA Special awards at Miss USA Notes 2026 Kayshauna Montaño West Springfield 28 Miss Hampshire County 2025 Perianne Caron Boston 26 Miss West End 2024 Melissa Sapini North Attleborough 21 Miss North Attleborough Top 10 Miss Photogenic Later Miss Universe Haiti 2025. 2023 Annika Sharma Newton 22 Miss Commonwealth Miss Photogenic Previously Miss Massachusetts Teen USA 2020 2022 Skarlet Ramirez Lawrence 27 Miss Lawrence Born in the Dominican Republic 2021 Sarah DeSouza Dracut 25 2020 Sabrina Victor Brockton 23 2019 Kelly O'Grady Cambridge 27 Later became correspondent for Fox Business 2018 Allissa Latham Lowell 26 Top 15 2017 Julia Scaparotti Peabody 24 New England Patriots Cheerleader 2016 Whitney Sharpe Burlington 21 2015 Polikseni Manxhari Boston 24 Born in Albania 2014 Caroline Lunny Holliston 22 Previously Miss Massachusetts Teen USA 2008 Top 15 at Miss Teen USA 2008. Contestant on The Bachelor (season 22), Bachelor in Paradise (season 5) and Bachelor in Paradise Australia (season 2) 2013 Sarah Kidd Leominster 20 Top 15 2012 Natalie Pietrzak Somerville 25 Sister of Monica Pietrzak, Miss Connecticut USA 2009 and Miss USA 2009 semifinalist 2011 Alida D'Angona Bolton 23 2010 Lacey Wilson Boston 26 Previously Miss Illinois Teen USA 2002 2009 Alison Michele Cronin East Weymouth 21 Previously Miss Massachusetts Teen USA 2005 2008 Jackie Bruno Assonet 23 Top 10, finishing in 10th place Previously Miss Massachusetts Teen USA 2003 3rd runner-up at Miss Teen USA 2003 2007 Despina Delios Lynn 23 2006 Tiffany Kelly Braintree 18 2005 Cristina Nardozzi Seekonk 21 Was contestant on Fear Factor in 2005 on the Miss USA episode #5.29 2004 Maria Lekkakos Rockport 25 2003 Susie Castillo Lawrence 23 Miss USA 2003 Top 15 semifinalist at Miss Universe 2003 Previously Miss Massachusetts Teen USA 1998 2002 Latoyia Cimone Foster Lowell 2001 Dana Tenille Powell Brookline 2000 Rosalie M. Allain Leominster Later Mrs. Massachusetts America 2009 under her married name, Rosalie Allain-Morris. 1999 Jennifer Krafve Saugus Mother of Avery Turner, Miss Massachusetts Teen USA 2024 1998 Shawnae Jebbia Mansfield 26 Miss USA 1998 Top 5 Finalist at Miss Universe 1998 1997 Jennifer K. Chapman Maynard 24 1996 Jacquelyn Doucette Lynnfield 26 Mother of Jillian Driscoll, Miss Massachusetts Teen USA 2022 1995 Kristen Mastroianni Wilbraham 23 Semi-finalist, finishing in 10th place Previously Miss Massachusetts Teen USA 1987 Top 10 at Miss Teen USA 1987 1994 Michelle Atamian Belmont 1993 Stacey Blaine Bellingham Miss Bellingham Miss Congeniality 1992 Christine Netishen Lowell 1991 Laura Wheeler Framingham 1990 Laureen Murphy Boston 1989 Kimberley Wallace Ipswich 1988 Anita Marie Lovely Franklin 1987 Rosanna Iversen Great Barrington Represented Massachusetts in Miss Oktoberfest 1987 1986 Sheila Benson Quincy 1985 Mercedes Waggoner Boston 21 Semi-finalist, finishing in 8th place 1984 Deborah Neary Onset 1983 Robin Jeanne Silva Swansea 1982 Janet Marie Flaherty Wilmington 24 Semi-finalist 1981 JoAnne Savery East Bridgewater Miss East Bridgewater Best State Costume 1980 Diane Campbell Melrose Miss Melrose 1979 Monica Patricia Magnus Boston 24 Semi-finalist 1978 Diane Elizabeth Pollard Hamilton 20 1st runner-up 1977 Carol Marcil Chelmsford 1976 Holly Ann Hoyle Attleboro 1975 Rilla Posson Natick 1974 Ethellean Hicks Roxbury 1973 Judith "Judy" Ann Gregory Boston 26 1972 Dale Carder Wellesley 1971 April Dow Amesbury 1970 Cheryl Stankiewicz Brockton Represented Massachusetts in the Miss World USA 1967 pageant 1969 Martha Cawley Needham 1968 Sonja Fritz Boston 1967 Pamela Procter Marblehead Daughter of Miss Massachusetts 1940 Polly Connors, 3rd Runner-Up to Miss America. 1966 Nancy Joan Brackett Brighton 20 Semi-finalist Semifinalist in Miss USA World 1963 as Miss Boston, MA 1965 Mary Lou Volpe Braintree 1964 Barbara Helen Robery Boston 1963 Sandra "Su-Su" Smith Newton Upper Falls 23 Semi-finalist Non-finalist at Miss World USA 1961 1962 Gale Pope Wellesley 1961 Elaine Cusick Hyde Park 18 Semi-finalist photograph 1960 Barbara Gale Feldman Natick 20 Top 15 1959 Beatrice Duprey Weymouth Also competed in the 1960 Miss Sun Fun USA Pageant 1958 Sally Ann Freedman Peabody Finalist in the 1961 Miss Sun Fun USA Pageant 1957 Sandra Ramsey Haverhill 19 Semi-finalist 1956 Elaine Murphy Weston 1955 Jean Dernago Springfield 1954 Nan Cowan Sterling 1953 Joan Daly Somerville 1952 Vel Dorne Boston 1 Age at the time of the Miss USA pageant
References
External links Official Website