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Roy Crawford - Superintendent

Roy is pleased to have the opportunity to serve the students, parents, staff and community of Vinalhaven.  From 1977-1989 he was a teacher and coach at Mattanawcook Academy in Lincoln and teacher, coach, assistant principal and athletic director at York High School in York, Maine.  He served as principal of Monmouth Academy in Monmouth, Maine from 1989-2001 as well as Superintendent of the Monmouth Schools from 1991-2001. In 2001 he left Maine and spent two years as Director of the Bonn International School in Bonn, Germany, followed by six years as superintendent in Manitou Springs, Colorado, and then seven years as a Head of School in Phnom Penh, Cambodia and the Island of Malta.

In June 2016, Roy and his wife Carrie returned to their home in Monmouth and settled back into life in Maine and are quite excited to return to school leadership in Maine, especially to such a unique and vital school and location.

Roy has a Bachelor Degree in English Education from Indiana University of Pennsylvania, a Master’s degree in school leadership from USM, and a Certificate of Advanced Study in the superintendency from UMO.  He has two adult children and five grandchildren, three of who are now in the Monmouth schools.  He and Carrie enjoy hiking, snowshoeing, traveling, camping, and watching the grandchildren’s activities. 

Ann Kirkpatrick - Principal

As a Maine native, Ann C. Kirkpatrick was reared in Caribou. In 1996, she moved to the Mid-coast of Maine and calls the Belfast area home.  Ann’s advanced education began at Springfield College (1981-1985) where she obtained a Bachelor or Science degree in Physical Education and Health with a teaching certification for Grades K through 12. In 1995, she obtained a Master’s degree in Educational Leadership at the University of Maine in Orono. Continuing her education at the University of Maine (Orono), Ann completed a Certificate of Advanced Studies in Educational Leadership with credentials for Superintendent Certification in 2009. Since that time, she remains current with appropriate certifications in teaching and administration.


Ann’s educational career began in Limestone, Maine teaching physical education and swimming. She coached and/or officiated soccer, basketball, track and softball. Additionally, Ann served as an athletic director for three years and more recently spent 4 years serving as a District Superintendent.


With 22 years of experience as a school administrator, Ann returns to the principalship where she is excited to begin this educational adventure in Vinalhaven at the Pre-Kindergarten-12 school!  She looks forward to the opportunity of working with every grade (PreK-12) in one school and discovering what makes Vinalhaven a unique and great place to learn. If her office door is open, please stop by and say, “Hello”.


In her time away from school, Ann enjoys working in her yard, biking, hiking, curling and cheering for all the New England sport’s teams! Go Red Sox!!


Deborah Bailey - Special Education Co-Director

Born in Australia and raised in New England, Deb has called Maine her home since arriving in Waterville for her senior year of high school. She graduated with her Bachelor’s Degree in Elementary and Special Education from Lesley College in Cambridge, Massachusetts. Deb moved to Rockland in 1988 and began teaching special education for MSAD 5.  She taught students from kindergarten to 12th grade during her 20-year career in Rockland. After completing her Master’s degree in Special Education Administration at the University of Maine, Orono, she was hired as the Assistant Special Education Director in Camden.  Deb became the Special Education Director in Union 69 (Hope, Appleton, Lincolnville) in 2011.  Her love of the ocean (as a former stern man) drew her first to the island of Chebeague where she oversees the special education program and now to Vinalhaven. She enjoys “rockhounding” for gems in the Western Foothills of Maine, gardening, hiking and reading.

Anna Perkins - Special Education Co-Director


Anna is excited to be working with the Vinalhaven School community this year.  She has lived in Maine working in the field of special education since 1980 in both public schools and private special purpose school settings as a teacher, consultant and special education administrator. Prior to that, Anna  worked in Massachusetts as a teacher and adjunct faculty in the fields of early childhood and school age special education. Anna holds a Bachelor’s degree in Education from Northeastern University and a Master’s in Special Education from Lesley College. Over the years, she  has been active in the special education community in Maine both at the local and state levels. Anna has always enjoyed working with families, students and staff and welcomes the opportunity to do so again this year at Vinalhaven School.  Anna’s two adult children live in Maine with their families. Favorite pastimes include family gatherings, outside activities, reading, knitting and learning new skills…such as soapmaking!