Stephen Holland was born in Bryn Mawr, PA. He began drawing and painting at the age of seven and has as he says "right brained it" his entire life. He is a graduate of Winthrop High School and was a recipient of the United Nations Art Award. Stephen went on to study at New England School of Art becoming a Dean's List Student. Summers were spent between Prout's Neck painting the Maine Coast and Cape Cod doing pastel portraits on the street where he "paid his dues" and was compelled to observe and draw quickly and accurately.

On completion of his studies, he worked as an Illustrator for a packaging firm and became Creative Director at the age of 25. After 12 years in the business, Stephen moved on to freelancing and teaching.

Stephen is a member of the Copley Society of Art, The New England Watercolor Society, The Cape Cod Art Association, The Plymouth Guild, The North River Arts Society and won the North River Arts Festival, W.T. Drawing Award.