Cynthia Winings was born in Reading, Pennsylvania. She received her Bachelors in Fine Arts from Moore College of Art and Design in Philadelphia. She earned her Masters degree in Fine Arts from Brooklyn College in 2003. On completing her degree, she began teaching as an Adjunct Professor of Art at Adelphi University and worked as the Graduate Assistant to the Deputy at Brooklyn College. She and her family moved to Brooklin, Maine from Brooklyn, New York in the fall of 2010. The Cynthia Winings Gallery was opened in June, 2013 and is one of the most dynamic and engaging art spaces in Maine. Winings has exhibited in solo and group exhibitions in New York, in the State of Maine, nationally and internationally.
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