Connolly is a realist painter who is  known for his local architectural subjects as well as New York City and beyond. Connolly participated in the Maine College of Art Baie Ste. Marie residency program in New Edinburg, Nova Scotia. He exhibited in the 2011 Portland Museum of Art Biennial Exhibition, and the 2010 Center for Maine Contemporary Art Biennial Exhibition. He is the recipient of a Pollock-Krasner Foundation Grant and the Sheldon Bergh Award. His work is in many private and corporate collections.